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Nomenclature of Flavonoids

(IUPAC Provisional Recommendations)*

Amlia P. Rauter1, Bernardo J. Herold2, Derek Horton3, Gerard Moss4, Ida Schomburg5, KarlHeinz Hellwich6, Marcus Ennis7

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Universidade de Lisboa, Faculdade de Cincias, Departamento de Qumica e Bioqumica/Centro de


Qumica e Bioqumica, Ed. C8, Piso 5, Campo Grande, 1749-016 Lisboa, Portugal; 2Universidade de
Lisboa, Instituto Superior Tcnico, Av. Rovisco Pais, 1041-001 Lisboa, Portugal; 3American University,
Department of Chemistry, Washington, D.C. 4400 Massachusetts Avenue NW, Washington, DC 20016, USA;
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School of Biological and Chemical Sciences, Queen Mary, University of London, Mile End Road, London
E1 4NS, UK; 5Technische Universitt Braunschweig, Institut fr Biochemie, Biotechnologie und
Bioinformatik, Langer Kamp 19B, 38106 Braunschweig, Germany; 6Postfach 10 07 31, 63007 Offenbach,
Germany;7European Bioinformatics Institute, Wellcome Trust Genome Campus, Hinxton, Cambridge CB10
1SD, UK

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Abstract: Flavonoid structures, found in nature or obtained by synthesis, have become more and

more complex, and a guide for aglycone names is provided here to permit the construction of the
names for their polyglycosylated species with clarity and conciseness. A joint working party of
IUPAC/IUBMB members has prepared these recommendations, which establish rules for the
general nomenclature of flavonoids, providing examples of acceptable trivial names, and names
derived from trivial names, together with semi-systematic and fully systematic names that follow
the published IUPAC recommendations.

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CONTENTS

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Flv-0 Introduction

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Flv-1 Flavonoids Definitions and conventions

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Flv-1.1 Flavonoid classes with a C6-C3-C6 carbon framework

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Flv-1.1.1 Flavonoids

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Flv-1.1.1.1 Flavans

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Flv-1.1.1.2 Flavones and 3-hydroxyflavones (flavonols)

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Flv-1.1.1.3 Anthocyanidins/anthocyanins (anthocyanidin 3-glycosides)

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Flv-1.1.2 Isoflavonoids

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Flv-1.1.2.1 Isoflavans

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IUPAC

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Flv-1.1.2.2 Isoflavones

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Flv-1.1.3 Neoflavonoids

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Flv-1.1.3.1 Neoflavans

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Flv-1.1.3.2 Neoflavones

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Flv-1.1.4 Chalcones and dihydrochalcones

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Flv-1.1.5 Aurones

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Flv-1.1.6 Pterocarpans and their 3,4-didehydro derivatives (coumestans)

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Flv-1.2 Rotenoids

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Flv-1.3 Flavonolignans

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Flv-1.4 Biflavonoids and other flavonoid oligomers

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Flv-2 Guide to the construction of semi-systematic names

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Flv-2.1 Flavans, isoflavans, neoflavans and compounds derived from them

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Flv-2.1.1 Flavans

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Flv-2.1.1.1 Flavanaglycons

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Flv-2.1.1.2 Flavan glycosides

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Flv-2.1.1.3 Flavanones

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Flv-2.1.2 Isoflavans

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Flv-2.1.3 Neoflavans

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Flv-2.2 Flavones, isoflavones, neoflavones and compounds derived from them

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Flv-2.2.1 Flavones

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Flv-2.2.1.1 Flavone aglycons

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Flv-2.2.1.2 Flavone glycosides

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Flv-2.2.1.3 C-Glycosyl substituted flavones

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Flv-2.2.1.4 Flavonols and flavonol glycosides

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Flv-2.2.2 Isoflavones and isoflavone glycosides

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Flv-2.2.2.1 Isoflavone aglycons

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Flv-2.2.2.2 Isoflavone glycosides

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Flv-2.2.3 Neoflavones and neoflavone glycosides

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Flv-2.2.3.1 Neoflavone aglycons

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Flv-2.2.3.2 Neoflavone glycosides

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Flv-2.3 Chalcones and dihydrochalcones

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Flv-2.4 Aurones

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Flv-2.4.1 Aurone aglycons

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Flv-2.4.2 Aurone glycosides

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Flv-2.5 Anthocyanidins and anthocyanidin 3-glycosides (anthocyanins)

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Flv-2.5.1 Anthocyanidins

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Flv-2.5.2 Anthocyanins

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Flv-2.6 Flavonoids containing additional fused/spiro rings in their structures

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Flv-2.6.1 Flavones

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Flv-2.6.2 Chalcones

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Flv-2.6.3 Aurones

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Flv-2.6.4 Anthocyanidins/Anthocyanins

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Flv-2.6.5 Pterocarpans

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Flv-2.6.6 Rotenoids

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Flv-2.7 Flavonolignans

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Flv-2.8 Biflavonoids and other flavonoid oligomers

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MEMBERSHIP OF SPONSORING BODIES

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REFERENCES

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*Sponsoring bodies: IUPAC Division(VIII) of Chemical Nomenclature and Structure


Representation (IUPAC project # 2009-018-2-800) and IUPAC-IUBMB Joint Commission on
Biochemical Nomenclature

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IUPAC

Corresponding author: Amlia P. Rauter, Universidade de Lisboa, Faculdade de Cincias,


Departamento de Qumica e Bioqumica/Centro de Qumica e Bioqumica, Ed. C8, Piso 5, Campo Grande,
1749-016 Lisboa, Portugal. E-mail:aprauter@fc.ul.pt

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Flv-0 Introduction

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Flavonoids, including the parent cyclic structures and their O and Cglycosylated derivatives, are
natural or synthetic compounds that are structurally diverse, and many exhibit biological activity [15]. They are quoted in the literature by researchers in diverse specialized areas, including natural
product chemistry, organic synthesis, medicinal and food chemistry, biology, and biochemistry.
Different workers have used a variety of alternative names and naming systems for such
compounds, and trivial names are commonly used to simplify complex names. Semi-systematic
names derived from parent structures are very useful for naming flavonoids, and have been widely
used, but they often lead to misunderstandings. There is an urgent need to avoid ambiguity in the
naming of flavonoids by clarifying acceptable usage and limiting the variety of options to a
reasonable extent.

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These recommendations establish rules for the general nomenclature of flavonoids, providing
examples of acceptable trivial names, and names derived from trivial names, together with semisystematic and fully systematic names that follow the published IUPAC recommendations [6-8].
Class names for flavonoids, their parent structures, and the order of citation of primed or unprimed
locants are revisited and clarified. Names of O- and C-glycosylated derivatives follow established
carbohydrate nomenclature [9]. Semi-systematic names are based on the parent structures or their
functional parents. These are presented and illustrative examples are provided to avoid ambiguous
interpretations.

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Flv-1 Flavonoids Definition and conventions

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The term flavonoid is commonly used to include not only natural products, but also synthetic
compounds related to them. The structural feature of this family of compounds is based on
derivatives of a phenyl-substituted 1-phenylpropane possessing a C15 skeleton, except for the
rotenoids, which have a C16 skeleton but are also phenyl-substituted 1-phenylpropane derivatives,
and that of flavonolignans, whose structure is based on flavonoids condensed with C6-C3 lignan
precursors.

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The following carbon frameworks characterize the various flavonoid classes:

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Flv-1.1 Flavonoid classes with a C6-C3-C6 carbon framework

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These are classes of compounds having a C6-C3-C6 carbon framework which contains a 1benzopyran (chromene) ring system, in which the aromatic ring is defined as ring A and the pyran is
ring C, along with a benzenoid aromatic substituent on the pyran ring defined as ring B. Depending
on the position of the linkage of ring B to the 1-benzopyran (chromene) moiety, three different
classes can be assigned: flavonoids (Flv-1.1.1), isoflavonoids (Flv-1.1.2) and neoflavonoids (Flv1.1.3). The other flavonoid classes that have a structure with a C6-C3-C6 carbon framework are the
chalcones (Flv-1.1.4), the aurones (Flv-1.1.5) and the pterocarpans and their 3,4-didehydro
derivatives (coumestans) (Flv-1.1.6).
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Flv-1.1.1 Flavonoids

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The flavonoids (2-aryl-1-benzopyrans) are compounds with a skeleton of type 1.

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The oxidation state of ring C and its derivatization with hydroxy groups is used to classify
flavonoids into different categories, such as:

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Flv-1.1.1.1 Flavans

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Flavans include compounds derived from 1, as well as flavan-3-ols (compounds derived from 2)
and flavan-4-ones (compounds derived from 4), which are generically designated in the literature as
flavanols and flavanones, respectively. Compounds derived from 3 are flavan-3,4-diols, designated
leukoanthocyanidins because their structure can be considered as being derived from that of an
anthocyanidin (see Flv-1.1.1.3), specifically a 3,4-dihydroxy-1,2,3,4-tetrahydroanthocyanidin,
which renders such compounds colourless.

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Flv-1.1.1.2 Flavones and 3-hydroxyflavones (flavonols)

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Flavones and 3-hydroxyflavones (flavonols) are compounds derived from 5 and 6, respectively,
which possess a 2-phenyl-1-benzopyran-4-one (2-phenylchromen-4-one) skeleton. The term
flavonol is used as a class name for compounds derived from 6.

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Flv-1.1.1.3 Anthocyanidins/anthocyanins (anthocyanidin 3-glycosides)

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Anthocyanidins are compounds derived from 7, which contains a flavylium ion (2-phenyl-1benzopyranylium or 2-phenylchromenylium) as a core structure. Anthocyanidins display colours
from red to purple and, together with their glycosides, the anthocyanins, represent a large group of
plant pigments.

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Flv-1.1.2 Isoflavonoids

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The isoflavonoids (3-aryl-1-benzopyrans) are compounds derived from 8.

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Flv-1.1.2.1 Isoflavans

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Isoflavans are compounds which have the skeleton 8. They may be substituted.

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Flv-1.1.2.2 Isoflavones

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Isoflavones are compounds with skeleton 9, the 2,3-didehydro structure 8 with a carbonyl group at
position 4. They may be substituted.

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Flv-1.1.3 Neoflavonoids

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The neoflavonoids (4-aryl-1-benzopyrans) are compounds with parent structure 10.

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Flv-1.1.3.1 Neoflavans

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Neoflavans are compounds with skeleton 10. They may be substituted.

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Neoflavones are compounds with skeleton 11. They may be substituted.

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Flv-1.1.4 Chalcones and dihydrochalcones

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Chalcones are compounds derived from (2E)-1,3-diphenylprop-2-en-1-one (chalcone, compound


12). They are early intermediates in the biosynthesis of flavonoids, in which the pyran ring C has
not yet been formed, and are therefore biogenetically and structurally related to them.
Dihydrochalcones are compounds derived from 1,3- diphenylpropan-1-one (compound 13).
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Flv-1.1.5 Aurones

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Aurones are compounds derived from 14, which is based on (2Z)-2-(arylmethylidene)-1benzofuran-3(2H)-one.

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Flv.1.1.6 Pterocarpans and their 3,4-didehydro derivatives (coumestans)

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Pterocarpans are compounds derived from 15 and from their 3,4-didehydro derivatives 16
(coumestans). They may be substituted.

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Flv-1.2 Rotenoids

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Rotenoids comprise rotenanes which are compounds with skeleton 17 and rotenones with skeleton
18. They may be substituted.

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Flv-1.3 Flavonolignans

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Flavonolignans have structures based on flavonoids condensed with C6-C3 lignan precursors (see
Flv-2.7).

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Flv-1.4 Biflavonoids and other flavonoid oligomers

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Biflavonoid and other flavonoid oligomers, which occur widely in nature, are exemplified and
named in Section Flv-2.8.

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Flv-2 Guide to the construction of semi-systematic names

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This section illustrates the construction of semi-systematic names and examples are given, with
trivial names, if known, and the systematic names are added.

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Primed locants are placed immediately after the corresponding unprimed locants in a set arranged in
ascending order (R-0.2.4.2 in [6]).

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Flv-2.1 Flavans, isoflavans, neoflavans and compounds derived from them

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Names of flavans, isoflavans and neoflavans can be derived from the name of the respective parent
hydride (Figure 1). The presence of a characteristic group is denoted by a prefix or by a suffix
attached to the parent name. The suffix is used for the principal characteristic group(s) according to
the priority order given in R.4.1 [6].

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Figure 1. Parent hydrides of flavans (1), isoflavans (8) and neoflavans (10).

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Flv-2.1.1 Flavans

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Flv-2.1.1.1 Flavan aglycons

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Example 1:

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Semi-systematic name

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flavan

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2phenyl-3,4-dihydro-2H-1-benzopyran

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2-phenyl-3,4-dihydro-2H-chromene

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Flv-2.1.1.2 Flavan glycosides

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Example 2:

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(a)

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(c)

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Note: Saccharide moiety shown in Mills depiction (a), in a conformational form (b) and in abbreviated form [9] (c).

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Semi-systematic name

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(2S)-2,7-bis(-D-glucopyranosyloxy)-8-(2-hydroxyethyl)-4-methoxyflavan-5-ol

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(2S)-2- [2,7-bis(-D-glucopyranosyloxy)-4-methoxyphenyl]-8-(2-hydroxyethyl)-3,4-dihydro-2H-1benzopyran-5-ol

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(2S)-2-[2,7-bis(-D-glucopyranosyloxy)-4-methoxyphenyl]-8-(2-hydroxyethyl)-3,4-dihydro-2Hchromen-5-ol

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Example 3:

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(2S)-7-(-D-glucopyranosyloxy)-4-methoxy-8-(3-methylbut-2-en-1-yl)flavan-2-ol

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(2S)-2-hydroxy-4-methoxy-8-(3-methylbut-2-en-1-yl)flavan-7-yl -D-glucopyranoside

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Systematic names

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(2S)-2-(2-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-7ol

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(2S)-2-(2-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-chromen-7-ol

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Flv-2.1.1.3 Flavanones

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Example 4:

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flavan-4-one

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2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one

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2-phenyl-2,3-dihydro-4H-chromen-4-one

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(2S)-4,5,7-trihydroxyflavan-4-one

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Trivial name

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naringenin

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31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 12 of 53

319
320

Systematic names

321

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

322

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one

323
324
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Page 13 of 53

325

Example 6:

326

327
328

rP
Fo

329

Semi-systematic name

330

(2S)-4,5,7-trihydroxy-6,8-bis(3-methylbut-2-en-1-yl)flavan-4-one

331
332

Trivial names

333

6,8-diprenylnaringenin, lonchocarpol A, senegalensein

334
335

Note: The trivial name senegalesein is used in the Dictionary of Flavonoids [4] and is kept as such in the present
recommendations. In the literature the incorrect spelling senegalesien is found in some instances.

rR

ee

336

ev

337

Systematic names

338
339

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl) -6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-1benzopyran-4-one

340
341

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl) -6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen4-one

ie

342
343

On

Example 7:

344

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

345
346
347

Semi-systematic name

348

(2R,3R)-3-hydroxyflavan-4-one
13
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

349

Not: flavanon-3-ol (R-4.1, Table 10 [6]).

350
351

Systematic names

352

(2R,3R)-3-hydroxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one

353

(2R,3R)-3-hydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one

354
355
356

Example 8:

357
358

rR

ee

rP
Fo

359

Semi-systematic name

360

(2R,3R) -2,3-dihydroxy-4,7-dimethoxy-8-(3-methylbut-2-en-1-yl)flavan-4-one

361

ev

362

Systematic names

363
364

(2R,3R)-3-hydroxy-2-(2-hydroxy-4-methoxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-2,3dihydro-4H-1-benzopyran-4-one

365
366

(2R,3R)-3-hydroxy-2-(2-hydroxy-4-methoxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-2,3dihydro-4H-chromen-4-one

ie

On

367
368

Flv-2.1.2 Isoflavans

369

Example 9:

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 14 of 53

370

371
372

14
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Page 15 of 53

373

Semi-systematic name

374

(3S)-isoflavan-7-ol

375
376

Systematic names

377

(3S)-3-phenyl-7-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one

378

(3S)-3-phenyl-7-hydroxy-2,3-dihydro-4H-chromen-4-one

379
380
381

rP
Fo

Example 10:

382

(1:1)

383
384
385

Semi-systematic name

386

rac-2,4,5,7-tetrahydroxyisoflavan-4-one

Trivial name

389

()-dalbergioidin

388

ie

387

ev

rR

ee

390

On

391

Systematic names

392

rac-3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-4H-1-benzopyran-4-one

393

rac-3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

394
395

Flv-2.1.3 Neoflavans

396

Example 11:

397

15
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

398
399
400

Semi-systematic name

401

(4R)-neoflavan-7-ol

402

rP
Fo

403

Systematic names

404

(4R)-4-phenyl-3,4-dihydro-2H-1-benzopyran-7-ol

405

(4R)-4-phenyl-3,4-dihydro-2H-chromen-7-ol

ee

406
407

Flv-2.2 Flavones, isoflavones, neoflavones and compounds derived from them

408
409
410
411

Names of flavones, isoflavones and neoflavones can be derived from the names of the respective
functional parents (Figure 2) which already contain one carbonyl group as an implied suffix. When
substituents are among those characteristic groups with a lower priority than ketones, they have to
be cited as prefixes, according to Table 10, Section R-4.1 [6].

ev

rR

412

ie

413
414

11

Figure 2. Functional parents of flavones (5), isoflavones (9) and neoflavones (11). Neoflavones are also
known in the literature as 4-arylcoumarins.

ly

415
416

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 16 of 53

417
418
419
420
421

When the principal characteristic group has a higher priority than a ketone, according to Table 10,
Section R-4.1 [6], names of flavones, isoflavones and neoflavones are derived from the respective
flavan, isoflavan or neoflavan parent hydride. Such groups are radicals, ions, acids, acid derivatives
(anhydrides, esters, acyl halides, amides), nitriles, aldehydes and chalcogen analogues of aldehydes.

422
423
424

Flavones, isoflavones and neoflavones containing a substructure with more than one carbonyl group
are named systematically on the basis of the respective parent hydride modified by the appropriate
suffix, i.e. -dione, -trione, etc.
16
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Page 17 of 53

425

Flv-2.2.1 Flavones

426

Flv-2.2.1.1 Flavone aglycons

427

Example 12:

428

429
430

rP
Fo

431

Semi-systematic name

432

flavone

433
434

Systematic names

435

2-phenyl-4H-1-benzopyran-4-one

436

2-phenyl-4H-chromen-4-one

438

ev

437

rR

ee

Example 13:

ie

439

w
On

440
441
442

Semi-systematic name

443

4,5,7-trihydroxyflavone

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

444
445

Trivial name

446

apigenin

447
448
17
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

449

Systematic names

450

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

451

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

452
453

Example 14:

454

455
456

ee

rP
Fo

457

Semi-systematic name

458

3,5,7-trihydroxy-4-methoxyflavone

459

Trivial name

461

diosmetin

ie

462

ev

460

rR

463

Systematic names

464

5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one

465

5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

On

466
467

Example 15:

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 18 of 53

468

469
470
471
18
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Page 19 of 53

472

Semi-systematic name

473

2-(piperidin-1-yl)ethyl 3-methyl-4-oxoflav-2-ene-8-carboxylate

474
475

Not: 2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2,3-didehydroflavan-8-carboxylate because of rule RF8.1 on introduction of unsaturation in parent names ending with an[10].

476
477

Trivial name

478

flavoxate

479

Note: flavoxate is an International Nonproprietary Name (INN) for the anticholinergic drug.

480

rP
Fo

481

Systematic names

482

2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylate

483

2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate

484
485

Flv-2.2.1.2 Flavone glycosides

486

Example 16:

ev

rR

ee

487

ie

488
489
490

Semi-systematic name

491

7-(-D-glucopyranosyloxy)-4,5-dihydroxy-3-methoxyflavone

492
493

Trivial name

494

7-O--D-glucopyranosylchrysoeriol

ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

495
496

Systematic names

497

7-(-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one
19
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

498

7-(-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

499
500

Example 17:

501
OH
HO

HOH2C

CH3
OH
3'

OCH3
4'

O
7

2
5

OH

OH

OH
O

ee
HOH2C

OH
OH

(a)

ie

ev

rR

503

HO

HO

502

OH

HO

rP
Fo
504

(b)

505
506

Note: Saccharide moiety in Mills depiction (a) and in a conformational form (b).

508

ly

507

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
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43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 20 of 53

509

Semi-systematic name

510

7-{-D-glucopyranosyl-(12)--D-glucopyranosyl-(12)-[-L-rhamnopyranosyl-(16)]--Dglucopyranosyloxy}-3,5-dihydroxy-4-methoxyflavone

511
512
513

Trivial name

20
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Page 21 of 53

514
515

7-O-{-D-glucopyranosyl-(12)--D-glucopyranosyl-(12)-[-L-rhamnopyranosyl-(16)]--Dglucopyranosyl}diosmetin

516
517
518

Not: diosmetin 7--D-glucopyranosyl- (12) --D-glucopyranosyl- (12) - [-Lrhamnopyranosyl- (16)]--D-glucopyranoside (because it specifies the oxygen atom at position 7
twice)

519
520

Systematic names

521
522

7-{-D-glucopyranosyl-(12)--D-glucopyranosyl-(12)-[-L-rhamnopyranosyl-(16)]--Dglucopyranosyloxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one

523
524

7-{-D-glucopyranosyl-(12)--D-glucopyranosyl-(12)-[-L-rhamnopyranosyl-(16)]--Dglucopyranosyloxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

525

Example 18:

ee

526

rP
Fo

527

528
529

ie

ev

rR

530

Semi-systematic name

531

methyl (4,5-dihydroxy-4-oxoflav-2-en-7-yl 2-O-acetyl--D-glucopyranosid)uronate

532
533
534

Not: methyl (4,5-dihydroxy-4-oxo-2,3-didehydroflavan-7-yl 2-O-acetyl--Dglucopyranosid)uronate because of rule RF-8.1 on introduction of unsaturation in parent names
ending with an [10].

535
536
537

Not: methyl (4,5-dihydroxyflavon-7-yl 2-O-acetyl--D-glucopyranosid)uronate because doubled


suffixes such as on-7-yl (which is one + yl) are not permitted in IUPAC chemical
nomenclature.

ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

538
539

Trivial name

540

7-O-(methyl 2-O-acetyl--D-glucopyranosyluronate)apigenin

541
542

Not: methyl [apigenin 7-(2-O-acetyl--D-glucopyranosiduronate)] (because it specifies the oxygen


atom at position 7 twice)

21
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

543
544

Note: The general rule that a name cannot contain two suffixes can be sometimes infringed in carbohydrate
nomenclature, such as with yluronate in the trivial name (see 2-Carb-22 in [9]).

545
546

Systematic names

547
548

methyl [5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-acetyl--Dglucopyranosid]uronate

549
550

methyl [5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-acetyl--Dglucopyranosid]uronate

rP
Fo

551
552

Flv-2.2.1.3 C-Glycosyl substituted flavones

553
554
555
556

Compounds arising formally from the elimination of water from the anomeric hydroxy group and a
hydrogen atom bound to a carbon atom (thus creating a CC bond) are named using the appropriate
glycosyl group [8]. In the past they have been named as flavonoid Cglycosides, but this
terminology should not be used (2-Carb33.7 [9]).

ee

557
558

rR

Example 19:

559

ie

ev

560

On

561
562

Semi-systematic name

563

6-(-D-glucopyranosyl)-4,5,7-trihydroxyflavone

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 22 of 53

564
565

Trivial names

566

isovitexin

567

6-(-D-glucopyranosyl)apigenin

568

Not: 6-C--D-glucopyranosylapigenin

569
22
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Page 23 of 53

570

Systematic names

571

6-(-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

572

6-(-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

573
574

Example 20:

575

576
577

ee

rP
Fo

578

Semi-systematic name

579

6-(-D-glucopyranosyl)-4,5-dihydroxy-7-methoxyflavone

580
581

Trivial name

582

6-(-D-glucopyranosyl)-7-O-methylapigenin

ie

583

ev

rR

584

Systematic names

585

6-(-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

586

6-(-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

On

587
588

Example 21:

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

589

590
23
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

591
592

Semi-systematic name

593

6,8-di-(-L-arabinopyranosyl)-4,5,7-trihydroxyflavone

594
595

Trivial name

596

6,8-di-(-L-arabinopyranosyl)apigenin

597

Not: apigenin 6,8-di-C--L-arabinopyranoside

598

rP
Fo

599

Systematic names

600

6,8-di-(-L-arabinopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

601

6,8-di-(-L-arabinopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

ee

602
603

Example 22:

rR

604

ie

ev

605

On

606
607

Semi-systematic name

608

6-(-L-arabinopyranosyl)-8-(-D-glucopyranosyl)-3,4,5,7-tetrahydroxyflavone

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 24 of 53

609
610

Trivial names

611

isocarniloside

612

6-(-L-arabinopyranosyl)-8-(-D-glucopyranosyl)luteolin

613

Not: luteolin 6-C--L-arabinopyranosyl-8--D-glucopyranoside

614
24
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Page 25 of 53

615

Systematic names

616
617

6-(-L-arabinopyranosyl)-2-(3,4-dihydroxyphenyl)-8-(-D-glucopyranosyl)-5,7-dihydroxy-4H-1benzopyran-4-one

618
619

6-(-L-arabinopyranosyl)-2-(3,4-dihydroxyphenyl)-8-(-D-glucopyranosyl)-5,7-dihydroxy-4Hchromen-4-one

620
621

Example 23:

622

rP
Fo

623
624

rR

ee

625

Semi-systematic name

626

4,5,7-trihydroxy-6-[-D-rhamnopyranosyl-(16)--D-glucopyranosyl]flavone

627

ev

628

Trivial names

629

dulcinoside

630

6-[-D-rhamnopyranosyl-(16)--D-glucopyranosyl]apigenin

631

Not: 6-C- [6-O-(-D-rhamnopyranosyl)--D-glucopyranosyl]apigenin

ie
On

632
633

Systematic names

634
635

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[-D-rhamnopyranosyl-(16)--D-glucopyranosyl]-4H-1benzopyran-4-one

636
637

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[-D-rhamnopyranosyl-(16)--D-glucopyranosyl]-4Hchromen-4-one

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

638
639

Flv-2.2.1.4 Flavonols and flavonol glycosides

640

Example 24:

641
25
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

642
643
644

Semi-systematic name

645

3-hydroxyflavone

646

rP
Fo

647

Systematic name

648

3-hydroxy-2-phenyl-4H-chromen-4-one

649
650

Example 25:

651
CH3

OH
O

4'

HO

O
7

HO

HO

2
4

OH

CH3
O

OH

O
O

ie

OH

OH

OCH3

O
HO

ev

652

OH

OH

CH3
HO

rR

ee
O

653
654

Semi-systematic name

655
656

4-hydroxy-3-{4-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl]-[-L-rhamnopyranosyl-(12)][-L-rhamnopyranosyl-(16)]--D-galactopyranosyloxy}-7-(-L-rhamnopyranosyloxy)flavones

ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 26 of 53

657
658

Systematic names

659
660
661

3-{4-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-[-L-rhamnopyranosyl-(12)]-[-Lrhamnopyranosyl-(16)]--D-galactopyranosyloxy}-2-(4-hydroxyphenyl)-7-(-Lrhamnopyranosyloxy)-4H-1-benzopyran-4-one

662
663
664

3-{4-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-[-L-rhamnopyranosyl-(12)]-[-Lrhamnopyranosyl-(16)]--D-galactopyranosyloxy}-2-(4-hydroxyphenyl)-7-(-Lrhamnopyranosyloxy)-4H-chromen-4-one

665
26
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 27 of 53

666

Flv-2.2.2 Isoflavones and isoflavone glycosides

667

Flv-2.2.2.1 Isoflavone aglycons

668

Example 26:

669

670
671

rP
Fo

672

Semi-systematic name

673

isoflavone

674

ee

675

Systematic name

676

3-phenyl-4H-chromen-4-one

rR

677
678

Example 27:

ev

679

ie

680
681
682

Semi-systematic name

683

4,5,7-trihydroxyisoflavone

ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

684
685

Trivial name

686

genistein

687
688

Systematic names

689

5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

690

5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
27
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

691
692

Flv-2.2.2.2 Isoflavone glycosides

693

Example 28:

694

695

rP
Fo

696
697

Semi-systematic name

698

7-(-D-glucopyranosyloxy)-4,5-dihydroxyisoflavone

699
700

Trivial names

701

genistin

702

7-O-(-D-glucopyranosyl)genistein

ev

703

rR

ee

704

Systematic names

705

7-(-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

706

7-(-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

ie

707

Flv-2.2.3 Neoflavones and neoflavone glycosides

709

Flv-2.2.3.1 Neoflavone aglycons

710

Example 29:

ly

708

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 28 of 53

711

712
713
714

Semi-systematic name
28
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 29 of 53

715

neoflavone

716
717

Trivial name

718

4-phenylcoumarin

719
720

Systematic names

721

4-phenyl-2H-1-benzopyran-2-one

722

4-phenyl-2H-chromen-2-one

rP
Fo

723
724

Example 30:

725

726
727

729

4,6-dihydroxy-7-methoxyneoflavone

Semi-systematic name

ie

728

ev

rR

ee

730
731

Trivial name

732

melannin

On

733

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

734

Systematic names

735

6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2H-1-benzopyran-2-one

736

6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2H-chromen-2-one

737
738

Flv-2.2.3.2 Neoflavone glycosides

739

Example 31:
29
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

740

741
742
743

Semi-systematic name

744

7-(-D-glucopyranosyloxy)-8-methylneoflavone

745

rP
Fo

746

Trivial name

747

7-(-D-glucopyranosyloxy)-8-methyl-4-phenylcoumarin

748

ee

749

Systematic names

750

7-(-D-glucopyranosyloxy)-8-methyl-4-phenyl-2H-1-benzopyran-2-one

751

7-(-D-glucopyranosyloxy)-8-methyl-4-phenyl-2H-chromen-2-one

752

ev

rR

753

Flv-2.3 Chalcones and dihydrochalcones

754
755
756
757
758
759
760
761

There is ambiguity in the literature concerning the numbering of the carbon atoms in chalcone.
Most authors, following IUPAC rule C-313.2 [8] as applied with acylaryl ketones such as
acetophenone, have assigned primed numbers to atoms in the phenyl ring attached to the carbonyl
group, and unprimed numbers to atoms in the other phenyl group. Atoms of the ethene-1,2-diyl
linker have been designated and . Some authors have used a reverse system, assigning unprimed
numbers to the phenyl ring attached to the carbonyl group and primed numbers to the other phenyl
ring. [The latter usage correlates with the numbering scheme in the flavan parent structure (Flv1.1.1.1) that arises biosynthetically from a chalcone.]

762
763
764

Because of this ambiguity, the term chalcone has been restricted since 1993 to its use as a retained
name of Type 3, no substitution (R-9.1, table 27a, ref. 6), and individual substituted chalcones are
named systematically, based usually on (2E)-prop-2-en-1-one.

765
766
767
768
769

The Dictionary of Flavonoids [5] and other standard sources [ref. 1, for example] adhere
consistently to the numbering of chalcones according to IUPAC rule C-313.2, and the alternative
usage has been largely abandoned. Since the use of Greek letters as locants is now discouraged, it is
now proposed that the term chalcone as a functional parent be retained as a Type 2, Limited
substitution name. This allows substitution in the phenyl rings, except where a substituent has

ie

ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 30 of 53

30
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 31 of 53

770
771

priority over the carbonyl group, in which situation a fully systematic name is required (Examples
33, 34, and 35).

772
773

Example 32:

774

775
776

rP
Fo

777

Semi-systematic name

778

chalcone

779
780

Systematic name

781

(2E)-1,3-diphenylprop-2-en-1-one

782

ev

783

rR

ee

Example 33:

784

ie
On

785
786
787

Semi-systematic name

788

2,5-dihydroxy-4-(N,N-dimethylamino)chalcone

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

789
790

Systematic name

791

(2E)-1-(2,5-dihydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

792
793

Example 34:
31
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

794

795
796
797

Systematic name

798

4-[(1E)-3-oxo-3-phenylprop-1-en-1-yl]benzonitrile

799
800
801

rP
Fo

Example 35:

rR

ee

802
803
804

Systematic name

805

2-[(2E)-1-oxo-3-phenylprop-2-en-1-yl]benzoic acid

ie

ev

806
807

Example 36:

808

ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 32 of 53

809
810
811

Systematic name

812

1-(4-hydroxy-2-methoxyphenyl)-3-phenylpropan-1-one

813
814

Flv-2.4 Aurones

815

Flv-2.4.1 Aurone aglycons


32
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 33 of 53

816

Example 37:

817

818
819
820

Semi-systematic name

821

aurone

822

rP
Fo

823

Systematic name

824

(2Z)-2-benzylidene-1-benzofuran-3(2H)-one

ee

825
826

Example 38:

rR

827

ie

ev

828

829
830

Semi-systematic name

831

3,4,4,6-tetrahydroxyaurone

On

832
833

Trivial name

834

aureusidin

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

835
836

Systematic name

837

(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3(2H)-one

838
33
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

839

Flv-2.4.2 Aurone glycosides

840

Example 39:

841

842

rP
Fo

843

Semi-systematic name

844

6-(-D-glucopyranosyloxy)-4,4-dihydroxyaurone

845
846

Systematic name

847
848

(2Z)-6-(-D-glucopyranosyloxy)-4-hydroxy-2-[(4-hydroxyphenyl)methylidene]-1-benzofuran3(2H)-one

rR

ee

849
850

Flv-2.5 Anthocyanidins and anthocyanidin 3-glycosides (anthocyanins)

851

Flv-2.5.1 Anthocyanidins

852
853

Anthocyanidins contain a flavylium ion (2-phenylchromenylium, 2-phenyl-14-benzopyran-1ylium) as a parent structure.

ie

ev

854
855

Example 40:

On

856

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 34 of 53

857
858
859

Semi-systematic name

860

3,3,4,5,7-pentahydroxyflavylium

861
34
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 35 of 53

862

Trivial name

863

cyanidin

864
865

Systematic names

866

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-14-benzopyran-1-ylium

867

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromenylium

868

rP
Fo

869

Flv-2.5.2 Anthocyanins

870

Example 41:

871

872
873

ie

ev

rR

ee

874

Semi-systematic name

875

3-(-D-glucopyranosyloxy)-3,4,5,7-tetrahydroxyflavylium

876
877

Trivial name

878

3-O--D-glucopyranosylcyanidin

ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

879
880

Systematic names

881

2-(3,4-dihydroxyphenyl)-3-(-D-glucopyranosyloxy)-5,7-dihydroxy-14-benzopyran-1-ylium

882

2-(3,4-dihydroxyphenyl)-3-(-D-glucopyranosyloxy)-5,7-dihydroxychromenylium

883
884

Example 42:

885
35
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

OH
OH
3'

HO

4'

O
7
5

2
3

OH

O
OH

OH
O
OH
O
O

886
887

OH

rP
Fo

888

Semi-systematic name

889
890

3-{6-O-[(E)-3-(4-hydroxyphenyl)acryloyl]--D-glucopyranosyloxy}-3,4,5,7tetrahydroxyflavylium

891

ee

892

Trivial name

893

3-O-{6-O-[(2E)-3-(4-hydroxyphenyl)acryloyl]--D-glucopyranosyl}cyanidin

894

ev

rR

895

Systematic names

896
897

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]--Dglucopyranosyloxy}-14-benzopyran-1-ylium

898
899

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]--Dglucopyranosyloxy}chromenylium

ie

On

900
901

Example 43:

902

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 36 of 53

36
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 37 of 53

OH
OH
3'

HO

4'

O
2
3

7
5

OH

OH
O

OH
OH
O

OH

H3C

903
904

OH

rP
Fo
HO

905

Semi-systematic name

906

3-[-L-rhamnopyranosyl-(16)--D-glucopyranosyloxy]-3,4,5,7-tetrahydroxyflavylium

907
908

Trivial name

909

3-O--rutinosylcyanidin

910

ev

rR

ee

911

Systematic names

912
913

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[-L-rhamnopyranosyl-(16)--D-glucopyranosyloxy]14-benzopyran-1-ylium

914
915

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[-L-rhamnopyranosyl-(16)--Dglucopyranosyloxy]chromenylium

ie

916
917

On

Example 44:

918

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

919
920
37
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

921

Semi-systematic name

922

3,7-bis(-D-glucopyranosyloxy)-3,4,5-trihydroxyflavylium

923
924

Trivial name

925

3,7-di-O-(-D-glucopyranosyl)cyanidin

926
927

Note: The multiplicative prefix di is used with non-substituted substituents, but with substituted substituents bis
must be used (R-0.1.4 in [1]).

928

rP
Fo

929

Systematic names

930

2-(3,4-dihydroxyphenyl)-3,7-bis(-D-glucopyranosyloxy)-5-hydroxy-14-benzopyran-1-ylium

931

2-(3,4-dihydroxyphenyl)-3,7-bis(-D-glucopyranosyloxy)-5-hydroxychromenylium

ee

932
933

Flv-2.6 Flavonoids containing additional fused/spiro rings in their structures

934
935

Locants for additional rings must be double primed to prevent confusion with those for the phenyl
ring, which are already single primed.

rR

936

Flv-2.6.1 Flavones

938

Example 45:

ie

937

ev

939

w
On

940

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 38 of 53

941
942

Semi-systematic name

943

5-hydroxy-6,7-[methylenebis(oxy)]flavones

944
945

Systematic names

946

9-hydroxy-6-phenyl-8H-[1,3]dioxolo[4,5-g]chromen-8-one

947

9-hydroxy-6-phenylpyrano[2,3-f][1,3]benzodioxol-8-one
38
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 39 of 53

948
949

Flv-2.6.2 Chalcones

950

Example 46:

951

952
953

rP
Fo

954

Semi-systematic name

955

3,4-[methylenebis(oxy)]chalcone

ee

956
957

Systematic names

958

(2E)-3-(1,3-benzodioxol-5-yl)-1-phenylprop-2-en-1-one

rR

959

Flv-2.6.3 Aurones

961

Example 47:

ie

960

ev

962

w
On

963

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

964
965

Semi-systematic name

966

2-methoxy-2,21-dihydrofuro[2,3:6,7]aurone

967
968

Trivial name

969

castillene A

970
39
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

971

Systematic name

972

2-benzyl-2-methoxybenzo[1,2-b:3,4-b]difuran-3(2H)-one

973
974

Example 48:

975

rP
Fo

976
977
978

Semi-systematic name

979

3,4,4,5,6-pentahydroxy-3,6-dihydropyrano[2,3,4,5:2,21,1,2]aurone

980

Trivial name

982

crombenin

983

ev

rR

981

ee

984

Systematic name

985

4,4,6,6,7-pentahydroxy-1,4-dihydro-3H-spiro[1-benzofuran-2,3-[2]benzopyran]-3-one

ie

986

Flv-2.6.4 Anthocyanidins/Anthocyanins

988

Example 49:

On

987

989

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 40 of 53

990
991
40
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 41 of 53

992

Semi-systematic name

993

6-(3,4-dihydroxyphenyl)-3-(-D-glucopyranosyloxy)-4,7-dihydroxy-3,5dimethoxypyrano[4,3,2:4,4a,5]flavylium

994
995
996

Trivial name

997

vitisin A

998
999

rP
Fo

Systematic names

1000
1001

5-(3,4-dihydroxyphenyl)-3-(-D-glucopyranosyloxy)-8-hydroxy-2-(4-hydroxy-3,5dimethoxyphenyl)pyrano[4,3,2-de]-14-benzopyran-1-ylium

1002
1003

5-(3,4-dihydroxyphenyl)-3-(-D-glucopyranosyloxy)-8-hydroxy-2-(4-hydroxy-3,5dimethoxyphenyl)pyrano[4,3,2-de]chromenylium

ee

1004
1005

Example 50:

rR

1006

ie

ev

1007

On

1008
1009

Semi-systematic name

1010

3,4,7,8,9-pentahydroxy-6-oxo-6H-[1,5]dioxaphenaleno[43a,3,2:3,4,4a,5]flavylium

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

1011
1012

Trivial name

1013

rosacyanin B

1014
1015

Systematic name

1016

11-(3,4-dihydroxyphenyl)-4,5,8-trihydroxy-2H-1,6-dioxa-10-oxoniabenzo[cd]pyren-2-one
41
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

1017

Flv-2.6.5 Pterocarpans

1018
1019

Although simple pterocarpans are ring-closure products of isoflavonoids, systematic numbering is


used [8,11].

1020
1021

Note: Systematic numbering and names of the pterocarpan skeleton are given below:

1022

1023
1024

rP
Fo

1025

Systematic names

1026

(6aR,11aR)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c][1]benzopyran

1027

(6aR,11aR)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene

rR

ee

1028
1029

Example 51:

1030

ie

ev

1031
1032
1033

Semi-systematic name

1034

9-methoxypterocarpan-3-ol

ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 42 of 53

1035
1036

Trivial name

1037

(-)-medicarpin

1038
1039

Systematic names

1040

(6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c][1]benzopyran-3-ol

1041

(6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol
42
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 43 of 53

1042
1043

Example 52:

1044

1045
1046

rP
Fo

1047

Semi-systematic names

1048

3,9-dihydroxypterocarp-6a-en-6-one

1049

3,9-dihydroxycoumestan-6-one

1050
1051

Not: 3,9-dihydroxy-6a,11a-didehydropterocarpan-6-one, because of rule RF-8.1 on introduction of


unsaturation in parent names ending with an [10].

ee

1052
1053

Trivial name

1054

Coumestrol

ev

rR

1055
1056

Systematic names

1057

3,9-dihydroxy-6H-[1]benzofuro[3,2-c][1]benzopyran-6-one

1058

3,9-dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one

Flv-2.6.6 Rotenoids

1061

Example 53:

ly

1060

On

1059

ie

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

1062

1063
1064
1065

Semi-systematic name

1066

rotenane
43
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

1067
1068

Systematic names

1069

(6aS,12aS)-6,6a,12,12a-tetrahydro[1]benzopyrano[3,4-b][1]benzopyran

1070

(6aS,12aS)-6,6a,12,12a-tetrahydrochromeno[3,4-b]chromene

1071
1072

Example 54:

1073

1074
1075

ee

rP
Fo

1076

Semi-systematic name

1077

5-hydroxy-4,5,7-trimethoxyrotenan-4-one

1078
1079

Trivial name

1080

sermundone

ie

ev

rR

1081

1082

Systematic names

1083
1084

(6aS,12aS)-11-hydroxy-2,3,9-trimethoxy-6a,12a-dihydro[1]benzopyrano[3,4-b][1]benzopyran12(6H)-one

1085

(6aS,12aS)-11-hydroxy-2,3,9-trimethoxy-6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one

ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 44 of 53

1086
1087

Example 55:

1088

1089
44
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 45 of 53

1090
1091

Semi-systematic name

1092

(5R)-4,5-dimethoxy-5-(prop-1-en-2-yl) -4,5-dihydrofuro[2,3:7,8]rotenan-4-one

1093
1094

Trivial name

1095

(5R)-4,5-dimethoxy-5-(prop-1-en-2-yl)- 4,5-dihydrofuro[2,3:7,8]rotenone

1096

rP
Fo

1097

Systematic names

1098
1099

(2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydro[1]benzopyrano[3,4b]furo[2,3-h][[1]benzopyran]-6(6aH)-one

1100
1101

(2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3h]chromen-6(6aH)-one

ee

1102
1103

rR

Example 56:

1104

ie

ev

1105

On

1106
1107

Semi-systematic name

1108

(5R)-4,5-dimethoxy-5-(prop-1-en-2-yl)-4,5-dihydrofuro[2,3:7,8]roten-2-ene-21,4-dione

1109

Not: (5R)-4,5-dimethoxy-5-(prop-1-en-2-yl)-2,3-didehydro-4,5dihydrofuro[2,3:7,8]rotenane-21,4-dione, because of rule RF-8.1 on introduction of unsaturation


in parent names ending with an [10].

1110
1111

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

1112
1113

Systematic names

1114
1115

(2R)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2-dihydro[1]benzopyrano[3,4-b]furo[2,3h][[1]benzopyran]-6,12-dione
45
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

1116
1117

(2R)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2-dihydrochromeno[3,4-b]furo[2,3-h]chromene-6,12dione

1118
1119

Example 57:

1120

rP
Fo

1121
1122
1123

Semi-systematic name

1124

6,6-dimethyl-5,6-dihydro-4H-1,3-dioxolo[4,5:4,5]pyrano[2,3:7,8]rotenan-4-one

ee

1125
1126

Trivial name

1127

millettone

ev

rR

1128
1129

Systematic names

1130
1131

(5aS,12bS)-2,2-dimethyl-5a,12b-dihydro-2H-[1,3]dioxolo[4,5-g]pyrano[2,3-c:6,5f]bis[1]benzopyran-13(6H)-one

1132
1133

(5aS,12bS)-2,2-dimethyl-5a,12b-dihydro-2H-[1,3]dioxolo[4,5-g]pyrano[2,3-c:6,5-f]dichromen13(6H)-one

ie

On

1134
1135

Flv-2.7 Flavonolignans

1136

Example 58:

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 46 of 53

1137

1138
1139
46
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 47 of 53

1140

Semi-systematic name

1141
1142

(2R,3R,5R,6R)-3-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-5-(hydroxymethyl)-5,6dihydro[1,4]dioxino[2,3:3,4]flavan-4-one

1143

Trivial names

1144

silibinin, also called silybin

1145
1146

Systematic names

1147
1148

(2R,3R)-3-hydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4benzodioxin-6-yl]-2,3-dihydro-4H-1-benzopyran-4-one

1149
1150

(2R,3R)-3-hydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one

1151

ee

rP
Fo

1152

Flv-2.8 Biflavonoids and other flavonoid oligomers

1153
1154
1155
1156

Biflavonoids and other flavonoid oligomers have been widely reported in the flavonoid literature
[12-16] and are also included in the present recommendations. The recommended semi-systematic
names consider the terminal flavonoid as the preferred one that is substituted by the other
components. If the flavonoids are identical, the lower locant is linked to the higher one.

ev

rR

1157
1158

Example 59:

ie

1159

w
ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

1160
1161
1162

Semi-systematic name

1163

[(3R)-4-methoxyisoflavan-2,7-diol]-(34)-[(3S,4R)-4-methoxyisoflavan-2,7-diol]

1164
1165

Systematic names
47
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

1166
1167

(3S,4R)-4-{4-hydroxy-5-[(3R)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2-methoxyphenyl}3-(2-hydroxy-4-methoxyphenyl)-3,3-dihydro-2H-1-benzopyran-7-ol

1168
1169

(3S,4R)-4-{4-hydroxy-5-[(3R)-7-hydroxy-3,4-dihydro-2H-chromen-3-yl]-2-methoxyphenyl}-3-(2hydroxy-4-methoxyphenyl)-3,3-dihydro-2H-chromen-7-ol

1170
1171

Example 60:

1172
OCH3

rP
Fo
4'

H3CO

7
5

OH

2'

HO
O

OH

4' 3'

ee

OH

1173

OH

1174

rR

1175

Semi-systematic name

1176

[(2S)-5-hydroxy-4,7-dimethoxyflavan-4-one]-(26)-[(2S)-3,4,5,7-tetrahydroxyflavan-4-one]

ie

ev

1177
1178

Trivial name

1179

[(2S)-4,7-di-O-methylnaringenin]-(26)-[(2S)-3-hydroxynaringenin]

On

1180
1181

Systematic names

1182
1183

(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-{2-[(2S)-5-hydroxy-7-methoxy-4-oxo-3,4-dihydro2H-1-benzopyran-2-yl]-5-methoxyphenyl}-2,3-dihydro-4H-1-benzopyran-4-one

1184
1185

(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-{2-[(2S)-5-hydroxy-7-methoxy-4-oxo-3,4-dihydro2H-chromen-2-yl]-5-methoxyphenyl}-2,3-dihydro-4H-chromen-4-one

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 48 of 53

1186
1187

Example 61:

1188

48
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 49 of 53

OH
HO

2'

4'
3'

OH

7
5

OH

HO

OH

6
5

O
4

OH
O

4'

HO

O
7
6

3'

OH

2'
4'

1189

3'

OH

OH

OH

rP
Fo

1190
1191

Semi-systematic name

1192
1193

(3,4,5,7-tetrahydroxyflavone)-(26)-(3,4,5,7-tetrahydroxyflavone)-(26)-(3,4,5,7tetrahydroxyflavone)

ee

1194
1195

Systematic names

1196
1197
1198

2-{2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-6-yl]-3,4dihydroxyphenyl}-6-{2-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-3,4-dihydroxyphenyl}-5,7dihydroxy-4H-1-benzopyran-4-one

1199
1200
1201

2-{2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-6-yl]-3,4-dihydroxyphenyl}-6{2-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-3,4-dihydroxyphenyl}-5,7-dihydroxy-4H-chromen-4one

1202

Note: In order to facilitate interpretation of the systematic name, systematic numbering is given below:

ie

ev

rR

1203
OH
HO

OH

O HO

OH

6 7

ly

OH

1204

4
3

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

O
4

OH
O

HO

O
7
6

2
5

OH

OH

2
4

OH

OH

1205
1206
49
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

1207

Example 62:

1208

1209
1210

rP
Fo

1211

Semi-systematic name

1212

(5,7-dihydroxyflavone)-(4-epoxy-6)-(4,5,7-trihydroxyflavone)

1213
1214

Trivial name

1215

hinokiflavone

ee

1216

rR

1217

Systematic names

1218
1219

6-[4-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)4H-1-benzopyran-4-one

1220
1221

6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4Hchromen-4-one

ie

ev

1222
1223

Example 63:

On

1224

ly

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

Page 50 of 53

1225
1226
1227

Semi-systematic name

1228

[(3R)-2-methoxyisoflavan-3,7-diol]-(4-epoxy-4)-[(3R)-2-methoxyflavan-3,7-diol]

1229
1230
50
P.O. 13757, Research Triangle Park, NC (919) 485-8700

Page 51 of 53

1231

Trivial name

1232

biscyclolobin

1233
1234

Systematic names

1235

3,3-oxybis(3-hydroxy-2-methoxy-4,1-phenylene)bis[(3R)-3,4-dihydro-2H-1-benzopyran-7-ol]

1236

3,3-oxybis(3-hydroxy-2-methoxy-4,1-phenylene)bis[(3R)-3,4-dihydro-2H-chromen-7-ol]

1237
1238
1239

rP
Fo

Example 64:

1240
1241

ie

ev

rR

ee

1242

Semi-systematic name

1243

(3,4,5,7-tetrahydroxyflavone)-2-(28,82)-(3,4,5,7-tetrahydroxyflavone)

1244
1245

Trivial name

1246

Anhydrobartramiaflavone

ly

On

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60

IUPAC

1247
1248

Systematic names

1249
1250

15,16,25,27,35,36,45,47-octahydroxy-1,3(1,2)-dibenzena-2,4(2,8)-bis(4H-1benzopyrana)cyclotetraphane-24,44-dione

1251
1252

15,16,25,27,35,36,45,47-octahydroxy-1,3(1,2)-dibenzena-2,4(2,8)-di(4H-chromena)cyclotetraphane24,44-dione

1253
1254
51
P.O. 13757, Research Triangle Park, NC (919) 485-8700

IUPAC

1255

MEMBERSHIP OF SPONSORING BODIES

1256
1257
1258
1259
1260
1261
1262
1263
1264
1265
1266

Membership of the IUPAC Division (VIII) of Chemical Nomenclature and Structure Representation
for (a) the period 2010-2011; (b) 2012. (a) President Richard Hartshorn; Past-President Gerard
Moss; Secretary Ture Damhus; Titular Members Jonathan Brecher, Kirill Degtyarenko, Philip
Hodge, Alan Hutton, Jeff Leigh, Jeffery Wilson, Andrey Yerin; Associate Members Karl-Heinz
Hellwich, Jaroslav Kahovec, Ebbe Nordlander, Jzsef Nyitrai, Warren Powell, Jan Reedijk;
National Representatives: Sundarababu Baskaran, Abdul Jalil Miah, Patrick Moyna, Hiroshi Ogino,
Amlia Rauter, Ricardo Bicca de Alencastro.(b) President Richard Hartshorn; Vice-President KarlHeinz Hellwich; Secretary Ture Damhus; Titular members Michael Beckett; Ebbe Nordlander;
Warren Powell; Amlia P. Rauter; Hinnerk Rey; Antony Williams; Andrey Yerin; Associate
Members Kirill Degtyarenko; Philip Hodge; Alan Hutton; Jan Reedijk; Nigel Wheatley; Jeffrey
Wilson; National Representatives Vefa Ahsen; Itrat Anis; Sundarababu Baskaran; Gernot Eller;
Md. Hashem; Wei Huang; Jaroslav Kahovec; Lupituko Mkayula; Jzsef Nagy; Supawan
Tantayanon.

ie

ev

rR

ee

1267
1268
1269
1270
1271
1272
1273
1274
1275
1276
1277
1278
1279

Membership of the IUPAC-IUBMB Joint Commission on Biochemical Nomenclature for (a) the
period of 20102012; (b) present membership: (a)Chair Dietmar Schomburg; Secretary Richard
Cammack; Titular members Gerard Moss; Keith Tipton; Johannes Vliegenthart; Associate members
Kristian Axelsen; Ron Caspi; Athel Cornish-Bowden; Derek Horton. (b) Titular members NCIUBMB and JCBN Chair Gerard Moss; Secretary Richard Cammack; NC-IUBMB Ron Caspi;
Andrew McDonalds; Dietmar Schomburg; NC-IUBMB and JCBN: Kristian Axelsen; Keith Tipton;
JCBN: Markus Ennis; Associate members NC-IUBMB Ida Schomburg; Johannes Vliegenthart;
JCBN Athel Cornish-Bowden; Derek Horton; Karl-Heinz Hellwich; Ture Damhus; Amelia P.
Rauter.

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REFERENCES

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1. Flavonoids Chemistry, Biochemistry and Applications (.M.Andersen, K. R. Markham,


eds.), CRC Press, Taylor and Francis Group, Boca Raton (2006).

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2. The Science of Flavonoids (E. Grotewold, ed.), Springer, New York (2006).

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1287

3. Flavonoids and Related Compounds: Bioavailability and Function (J. P. E. Spencer, A.


Crozier, eds.), Oxidative Stress and Disease Series, Taylor and Francis, Boca Raton (2012).

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4. J. Buckingham. Dictionary of Flavonoids, Taylor and Francis, Boca Raton (2012).

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5. J. B. Harborne, H. Baxter. The Handbook of Natural Flavonoids (J. B. Harborne, H. Baxter,


eds.), Vols. 1 and 2, John Wiley, New York (1999).

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6. IUPAC. A Guide to IUPAC Nomenclature of Organic Compounds. R. Panico, W. H. Powell,


J.-C. Richer (Eds.), Blackwell Scientific Publications, Oxford (1993).

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1294

7. H. A. Favre, K.-H. Hellwich, G. P. Moss, W. H. Powell, J. G. Traynham, Corrections to 'A


Guide to IUPAC Nomenclature of Organic Compounds'. Pure Appl. Chem. 77, 1327 (1999).

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8. IUPAC Recommendations 1979. Nomenclature of Organic Chemistry (the 'Blue Book').


Sections A, B, C, D, E, F, H. Prepared for publication by J. Rigaudy and S. P. Klesney. S. P.
Klesney (Ed.), Pergamon Press, Oxford (1979).

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9. A. D. McNaught. Nomenclature of carbohydrates (IUPAC Recommendations 1996), Pure


Appl. Chem. 68, 1919 (1996).

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10. P. M. Giles, Jr. Section F:Natural Products and Related Compounds, Pure Appl. Chem. 71,
587 (1999); Corrections and modifications: H. A. Favre, P. M. Giles Jr., K.-H. Hellwich, A.
D. McNaught, G. P. Moss, W. H. Powell. Pure Appl. Chem. 76, 1283 (2004).

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12. H. Geiger, Biflavonoids and Triflavonoids, in The Flavonoids: Advances in Research since
1986 (J. B. Harborne, ed.), pp 95-115. Chapman & Hall, London (1994).

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13. H. Geiger, C. Quinn, Biflavonoids, in The Flavonoids: Advances in Research since 1980 (J.
B. Harborne, T. J. Mabry, eds.), pp. 99-124. Chapman & Hall, London (1988).

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1310

14. H. Geiger, C. Quinn, Biflavonoids, in The Flavonoids (J. B. Harborne, T. J. Mabry, eds.), pp.
505-534. Chapman & Hall, London (1982).

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15. H. Geiger, C. Quinn, Biflavonoids, in The Flavonoids (J. B. Harborne, T. J. Mabry, H.


Mabry, eds.), pp. 692-742. Chapman & Hall, London (1975).

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16. H. D. Lockley, Fortschr. Chem. Org. Naturst. 30, 207 (1973).

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G. P. Moss. Nomenclature of fused and bridged ring systems (IUPAC recommendations


1998), Pure Appl. Chem.70, 143 (1998).

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