Carotenoid

Carotenoids (/kəˈrɒtɪnɔɪd/), also called tetraterpenoids, are

yellow, orange, and red organic pigments that are produced by
plants and algae, as well as several bacteria, and fungi.[1]
Carotenoids give the characteristic color to pumpkins, carrots,
corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and
daffodils.[1] Carotenoids can be produced from fats and other basic
organic metabolic building blocks by all these organisms. The only
land dwelling arthropods known to produce carotenoids are
aphids, and spider mites, which acquired the ability and genes The orange ring surrounding Grand
from fungi.[2][3][4] It is also produced by endosymbiotic bacteria in Prismatic Spring is due to carotenoid
whiteflies.[5] Carotenoids from the diet are stored in the fatty molecules, produced by mats of
tissues of animals,[1] and exclusively carnivorous animals obtain cyanobacteria and other bacteria.
the compounds from animal fat. In the human diet, absorption of
carotenoids is improved when consumed with fat in a meal.[6]
Cooking carotenoid-containing vegetables in oil and shredding the vegetable both increase carotenoid
bioavailability.[1][6][7]

There are over 1,100 known carotenoids[8] which can be further categorized into two classes, xanthophylls
(which contain oxygen) and carotenes (which are purely hydrocarbons and contain no oxygen).[1] All are
derivatives of tetraterpenes, meaning that they are produced from 8 isoprene molecules and contain 40
carbon atoms. In general, carotenoids absorb wavelengths ranging from 400 to 550 nanometers (violet to
green light). This causes the compounds to be deeply colored yellow, orange, or red. Carotenoids are the
dominant pigment in autumn leaf coloration of about 15-30% of tree species,[1] but many plant colors,
especially reds and purples, are due to polyphenols.

Carotenoids serve two key roles in plants and algae: they absorb
light energy for use in photosynthesis, and they provide
photoprotection via non-photochemical quenching.[9] Carotenoids
that contain unsubstituted beta-ionone rings (including β-carotene,
α-carotene, β-cryptoxanthin, and γ-carotene) have vitamin A
activity (meaning that they can be converted to retinol). In the eye,
lutein, meso-zeaxanthin, and zeaxanthin are present as macular
pigments whose importance in visual function, as of 2016, remains
under clinical research.[1][10]

Contents
Biosynthesis
MEP pathway
Carotenoid biosynthetic pathway
Regulation Macular pigments of the human eye
Structure and function
Properties
Foods
Morphology
Oxygenation
Transport
Storage
Respiration
Synergetic modality
Physiological effects
Plant colors
Bird colors and sexual selection
Aroma chemicals
Disease
Naturally occurring carotenoids
See also
References
External links

Biosynthesis
The basic building blocks of carotenoids are isopentenyl
diphosphate (IPP) and dimethylallyl diphosphate (DMAPP).[11]
These two isoprene isomers are used to create various compounds
depending on the biological pathway used to synthesize the
isomers.[12] Plants are known to use two different pathways for
IPP production: the cytosolic mevalonic acid pathway (MVA) and
the plastidic methylerythritol 4-phosphate (MEP).[11] In animals,
the production of cholesterol starts by creating IPP and DMAPP
using the MVA.[12] For carotenoid production plants use MEP to
generate IPP and DMAPP.[11] The MEP pathway results in a 5:1
mixture of IPP:DMAPP.[12] IPP and DMAPP undergo several
reactions, resulting in the major carotenoid precursor,
geranylgeranyl diphosphate (GGPP). GGPP can be converted into
carotenes or xanthophylls by undergoing a number of different
steps within the carotenoid biosynthetic pathway.[11]

MEP pathway

Glyceraldehyde 3-phosphate and pyruvate, intermediates of

Pathway of carotenoid synthesis
photosynthesis, are converted to deoxy-D-xylulose 5-phosphate
(DXP) using the catalyst DXP synthase (DXS). DXP
reductoisomerase reduces and rearranges the molecules within
DXP[11] in the presence of NADPH,[12] forming MEP.[11] Next, MEP is converted to 4-(cytidine 5’-
diphospho)-2-C-methyl-D-erythritol (CDP-ME) in the presence of CTP via the enzyme MEP
cytidylyltransferase. CDP-ME is then converted, in the presence of ATP, to 2-phospho-4-(cytidine 5’-
diphospho)-2-C-methyl-D-erythritol (CDP-ME2P). The conversion to CDP-ME2P is catalyzed by the
enzyme CDP-ME kinase. Next, CDP-ME2P is converted to 2-C-methyl-D-erythritol 2,4-cyclodiphosphate
(MECDP). This reaction occurs when MECDP synthase catalyzes the reaction and CMP is eliminated
from the CDP-ME2P molecule. MECDP is then converted to (e)-4-hydroxy-3-methylbut-2-en-1-yl
diphosphate (HMBDP) via HMBDP synthase in the presence of flavodoxin and NADPH. HMBDP is
reduced to IPP in the presence of ferredoxin and NADPH by the enzyme HMBDP reductase. The last two
steps involving HMBPD synthase and reductase can only occur in completely anaerobic environments. IPP
is then able to isomerize to DMAPP via IPP isomerase.[12]

Carotenoid biosynthetic pathway

Two GGPP molecules condense via phytoene synthase (PSY),

forming the 15-cis isomer of phytoene. PSY belongs to the
squalene/phytoene synthase family and is homologous to squalene
synthase that takes part in steroid biosynthesis. The subsequent
conversion of phytoene into all-trans-lycopene depends on the
organism. Bacteria and fungi employ a single enzyme, the bacterial
phytoene desaturase (CRTI) for the catalysis. Plants and
cyanobacteria however utilize four enzymes for this process.[13]
The first of these enzymes is a plant-type phytoene desaturase
which introduces two additional double bonds into 15-cis-
phytoene by dehydrogenation and isomerizes two of its existing The conversion of phytoene to
double bonds from trans to cis producing 9,15,9’-tri-cis-ζ-carotene. lycopene in plants and cyanobacteria
The central double bond of this tri-cis-ζ-carotene is isomerized by (left) differs compared to bacteria
the zeta-carotene isomerase Z-ISO and the resulting 9,9'-di-cis-ζ- and fungi (right).
carotene is dehydrogenated again via a ζ-carotene desaturase
(ZDS). This again introduces two double bonds, resulting in
7,9,7’,9’-tetra-cis-lycopene. CRTISO, a carotenoid isomerase, is needed to convert the cis-lycopene into an
all-trans lycopene in the presence of reduced FAD.

This all-trans lycopene is cyclized; cyclization gives rise to carotenoid diversity, which can be distinguished
based on the end groups. There can be either a beta ring or an epsilon ring, each generated by a different
enzyme (lycopene beta-cyclase [beta-LCY] or lycopene epsilon-cyclase [epsilon-LCY]). α-Carotene is
produced when the all-trans lycopene first undergoes reaction with epsilon-LCY then a second reaction
with beta-LCY; whereas β-carotene is produced by two reactions with beta-LCY. α- and β-Carotene are the
most common carotenoids in the plant photosystems but they can still be further converted into
xanthophylls by using beta-hydrolase and epsilon-hydrolase, leading to a variety of xanthophylls.[11]

Regulation

It is believed that both DXS and DXR are rate-determining enzymes, allowing them to regulate carotenoid
levels.[11] This was discovered in an experiment where DXS and DXR were genetically overexpressed,
leading to increased carotenoid expression in the resulting seedlings.[11] Also, J-protein (J20) and heat
shock protein 70 (Hsp70) chaperones are thought to be involved in post-transcriptional regulation of DXS
activity, such that mutants with defective J20 activity exhibit reduced DXS enzyme activity while
accumulating inactive DXS protein.[14] Regulation may also be caused by external toxins that affect
enzymes and proteins required for synthesis. Ketoclomazone is derived from herbicides applied to soil and
binds to DXP synthase.[12] This inhibits DXP synthase, preventing synthesis of DXP and halting the MEP
pathway.[12] The use of this toxin leads to lower levels of carotenoids in plants grown in the contaminated
soil.[12] Fosmidomycin, an antibiotic, is a competitive inhibitor of DXP reductoisomerase due to its similar
structure to the enzyme.[12] Application of said antibiotic prevents reduction of DXP, again halting the
MEP pathway. [12]

Structure and function

The structure of carotenoids allows for biological abilities,
including photosynthesis, photoprotection, plant coloration, and
cell signaling.
General structure of a carotenoid:
The general structure of the carotenoid is a polyene chain polyene tail with double bonds,
consisting of 9-11 double bonds and possibly terminating in rings. possible terminal rings
This structure of conjugated double bonds leads to a high reducing
potential, or the ability to transfer electrons throughout the
molecule.[15] Carotenoids can transfer excitation energy in one of two ways: 1) singlet-singlet energy
transfer from carotenoid to chlorophyll, and 2) triplet-triplet energy transfer from chlorophyll to carotenoid.
The singlet-singlet energy transfer is a lower energy state transfer and is used during photosynthesis.[16]
The length of the polyene tail enables light absorbance in the photosynthetic range; once it absorbs energy
it becomes excited, then transfers the excited electrons to the chlorophyll for photosynthesis.[15] The triplet-
triplet transfer is a higher energy state and is essential in photoprotection.[16] Light produces damaging
species during photosynthesis, with the most damaging being reactive oxygen species (ROS). As these
high energy ROS are produced in the chlorophyll the energy is transferred to the carotenoid’s polyene tail
and undergoes a series of reactions in which electrons are moved between the carotenoid bonds in order
find the most balanced state (lowest energy state) for the carotenoid.[15]

The length of carotenoids also has a role in plant coloration, as the length of the polyene tail determines
which wavelengths of light the plant will absorb. Wavelengths that are not absorbed are reflected and are
what we see as the color of a plant.[15] Therefore, differing species will contain carotenoids with differing
tail lengths allowing them to absorb and reflect different colors.[15]

Carotenoids also participate in different types of cell signaling.[16] They are able to signal the production of
absicisic acid, which regulates plant growth, seed dormancy, embryo maturation and germination, cell
division and elongation, floral growth, and stress responses.[17]

Properties
Carotenoids belong to the category of tetraterpenoids (i.e., they
contain 40 carbon atoms, being built from four terpene units each
containing 10 carbon atoms). Structurally, carotenoids take the
form of a polyene hydrocarbon chain which is sometimes
terminated by rings, and may or may not have additional oxygen
atoms attached.

Carotenoids with molecules containing oxygen, such as

lutein and zeaxanthin, are known as xanthophylls.
The unoxygenated (oxygen free) carotenoids such as α-
carotene, β-carotene, and lycopene, are known as
carotenes. Carotenes typically contain only carbon and
hydrogen (i.e., are hydrocarbons), and are in the Gac fruit, rich in lycopene
subclass of unsaturated hydrocarbons.
Their color, ranging from pale yellow through bright orange to
deep red, is directly linked to their structure. Xanthophylls are
often yellow, hence their class name. The double carbon-carbon
bonds interact with each other in a process called conjugation,
which allows electrons in the molecule to move freely across these
areas of the molecule. As the number of conjugated double bonds
increases, electrons associated with conjugated systems have more
room to move, and require less energy to change states. This
causes the range of energies of light absorbed by the molecule to Ingesting carotenoid-rich foods
decrease. As more wavelengths of light are absorbed from the affects the plumage of flamingos.
longer end of the visible spectrum, the compounds acquire an
increasingly red appearance.

Carotenoids are usually lipophilic due to the presence of long unsaturated aliphatic chains as in some fatty
acids. The physiological absorption of these fat-soluble vitamins in humans and other organisms depends
directly on the presence of fats and bile salts.[1]

Foods
Beta-carotene, found in pumpkins, sweet potato, carrots and winter squash, is responsible for their orange-
yellow colors.[1] Dried carrots have the highest amount of carotene of any food per 100-gram serving,
measured in retinol activity equivalents (provitamin A equivalents).[18] Vietnamese gac fruit contains the
highest known concentration of the carotenoid lycopene.[19] Although green, kale, spinach, collard greens,
and turnip greens contain substantial amounts of beta-carotene.[1] The diet of flamingos is rich in
carotenoids, imparting the orange-colored feathers of these birds.[20]

Morphology
Carotenoids are located primarily outside the cell nucleus in different cytoplasm organelles, lipid droplets,
cytosomes and granules. They have been visualised and quantified by raman spectroscopy in an algal
cell.[21]

With the development of monoclonal antibodies to trans-lycopene it was possible to localise this carotenoid
in different animal and human cells.[22][23]

Oxygenation
Carotenoids play an important role in biological oxygenation. In plant cells they are involved in the control
of trans-membrane transport of molecular oxygen released in photosynthesis.[24][25]

In animals carotenoids play an important role to support oxygen in its transport, storage and metabolism.

Transport

Carotenoids are hydrophobic and are typically present in plasma lipoproteins and cellular lipid
structures.[26] Since molecular oxygen is also a hydrophobic molecule, lipids provide a more favorable
environment for O2 solubility than in aqueous mediums.[27][28] By protecting lipids from free-radical
damage, which generate charged lipid peroxides and other oxidised derivatives, carotenoids support
crystalline architecture and hydrophobicity of lipoproteins and cellular lipid structures, hence oxygen
solubility and its diffusion therein.[29][30]

Storage

It was first suggested that carotenoids can be involved in the intracellular depot of oxygen in 1973 by V.N.
Karnaukhov.[28] Later it was discovered that carotenoids can also stimulate the formation of intracellular
lipid droplets, which can store additional molecular oxygen.[31] These properties of carotenoids help
animals to adapt to environmental stresses, high altitude, intracellular infections and other
hypoxicconditions.[32][33]

Respiration

Carotenoids, by increasing oxygen diffusion and the oxygen carrying capacity of plasma lipoproteins, can
stimulate oxygen delivery into body tissues. This improves tissue and cellular oxygenation and stimulates
the growth and respiration of mitochondria.[34][35]

Synergetic modality

Oxygen is required in many intracellular reactions including hydroxylation, which is important for
metabolic activation of prodrugs and prohormones, such as vitamin D3. Carotenoids not only provide
support for intracellular oxygenation but can also improve efficacy of these molecules.

Carotenoids can form physical complexes with different molecules. With hydrophobic molecules this could
be self-assembly. With amphiphilic or hydrophilic compounds the use of lycosome or supercritical CO2
technologies, or other methods, are required.[35]][36] Carotenoids in these complexes provide a new
modality of supporting and boosting tissue oxygenation, which could be synergistically beneficial to the
therapeutic objectives of different nutraceutical or pharmaceutical molecules.[36][37]

Physiological effects
Reviews of epidemiological studies seeking correlations between carotenoid consumption in food and
clinical outcomes have come to various conclusions:

A 2015 review found that foods high in carotenoids appear to be protective against head and
neck cancers.[38]
Another 2015 review looking at whether caretenoids can prevent prostate cancer found that
while several studies found correlations between diets rich in carotenoids appeared to have
a protective effect, evidence is lacking to determine whether this is due to carotenoids per
se.[39]
A 2014 review found no correlation between consumption of foods high in carotenoids and
vitamin A and the risk of getting Parkinson's disease.[40]
Another 2014 review found no conflicting results in studies of dietary consumption of
carotenoids and the risk of getting breast cancer.[41]

Carotenoids are also important components of the dark brown pigment melanin, which is found in hair,
skin, and eyes. Melanin absorbs high-energy light and protects these organs from intracellular damage.
 Several studies have observed positive effects of high-carotenoid diets on the texture, clarity,
color, strength, and elasticity of skin.[42][43][44]
A 1994 study noted that high carotenoid diets helped reduce symptoms of eyestrain (dry
eye, headaches, and blurred vision) and improve night vision.[45][46]

Humans and other animals are mostly incapable of synthesizing carotenoids, and must obtain them through
their diet. Carotenoids are a common and often ornamental feature in animals. For example, the pink color
of salmon, and the red coloring of cooked lobsters and scales of the yellow morph of common wall lizards
are due to carotenoids.[47] It has been proposed that carotenoids are used in ornamental traits (for extreme
examples see puffin birds) because, given their physiological and chemical properties, they can be used as
visible indicators of individual health, and hence are used by animals when selecting potential mates.[48]

Plant colors
The most common carotenoids include lycopene and the vitamin A
precursor β-carotene. In plants, the xanthophyll lutein is the most
abundant carotenoid and its role in preventing age-related eye
disease is currently under investigation.[10] Lutein and the other
carotenoid pigments found in mature leaves are often not obvious
because of the masking presence of chlorophyll. When chlorophyll
is not present, as in autumn foliage, the yellows and oranges of the
carotenoids are predominant. For the same reason, carotenoid
colors often predominate in ripe fruit after being unmasked by the Yellow and orange leaf colors in
disappearance of chlorophyll. autumn are due to carotenoids,
which are visible after chlorophyll
Carotenoids are responsible for the brilliant yellows and oranges degrades for the season.
that tint deciduous foliage (such as dying autumn leaves) of certain
hardwood species as hickories, ash, maple, yellow poplar, aspen,
birch, black cherry, sycamore, cottonwood, sassafras, and alder.
Carotenoids are the dominant pigment in autumn leaf coloration of
about 15-30% of tree species.[49] However, the reds, the purples,
and their blended combinations that decorate autumn foliage
usually come from another group of pigments in the cells called
anthocyanins. Unlike the carotenoids, these pigments are not
present in the leaf throughout the growing season, but are actively
produced towards the end of summer.[50]

Bird colors and sexual selection

Dietary carotenoids and their metabolic derivatives are responsible
for bright yellow to red coloration in birds.[51] Studies estimate that
around 2956 modern bird species display carotenoid coloration
and that the ability to italicize these pigments for external
coloration has evolved independently many times thought avian Apricots, rich in carotenoids
evolutionary history.[52] Carotenoid coloration exhibits high levels
of sexual dimorphism, meaning that male birds tend to display
more vibrant coloration than females of the same species.[53]
These differences arise due to the selection of yellow and red coloration in males by female
preference.[54][53] In many species of birds, females invest greater time and resources into raising offspring
than their male partners. Therefore, it is imperative that female birds carefully select high quality mates.
Current literature supports the theory that vibrant carotenoid coloration is correlated with male quality—
either though direct effects on immune function and oxidative stress,[55][56][57] or through a connection
between carotenoid metabolizing pathways and pathways for cellular respiration.[58][59]

Aroma chemicals
Products of carotenoid degradation such as ionones, damascones and damascenones are also important
fragrance chemicals that are used extensively in the perfumes and fragrance industry. Both β-damascenone
and β-ionone although low in concentration in rose distillates are the key odor-contributing compounds in
flowers. In fact, the sweet floral smells present in black tea, aged tobacco, grape, and many fruits are due to
the aromatic compounds resulting from carotenoid breakdown.

Disease
Some carotenoids are produced by bacteria to protect themselves from oxidative immune attack. The
aureus (golden) pigment that gives some strains of Staphylococcus aureus their name is a carotenoid called
staphyloxanthin. This carotenoid is a virulence factor with an antioxidant action that helps the microbe
evade death by reactive oxygen species used by the host immune system.[60]

Naturally occurring carotenoids

Hydrocarbons
Lycopersene 7,8,11,12,15,7',8',11',12',15'-Decahydro-γ,γ-carotene
Phytofluene
Lycopene
Hexahydrolycopene 15-cis-7,8,11,12,7',8'-Hexahydro-γ,γ-carotene
Torulene 3',4'-Didehydro-β,γ-carotene
α-Zeacarotene 7',8'-Dihydro-ε,γ-carotene
α-Carotene
β-Carotene
γ-Carotene
δ-Carotene
ε-Carotene
ζ-Carotene
Alcohols
Alloxanthin
Bacterioruberin 2,2'-Bis(3-hydroxy-3-methylbutyl)-3,4,3',4'-tetradehydro-1,2,1',2'-
tetrahydro-γ,γ-carotene-1,1'-diol
Cynthiaxanthin
Pectenoxanthin
Cryptomonaxanthin (3R,3'R)-7,8,7',8'-Tetradehydro-β,β-carotene-3,3'-diol
Crustaxanthin β,-Carotene-3,4,3',4'-tetrol
Gazaniaxanthin (3R)-5'-cis-β,γ-Caroten-3-ol
 OH-Chlorobactene 1',2'-Dihydro-f,γ-caroten-1'-ol
Loroxanthin β,ε-Carotene-3,19,3'-triol
Lutein (3R,3′R,6′R)-β,ε-carotene-3,3′-diol
Lycoxanthin γ,γ-Caroten-16-ol
Rhodopin 1,2-Dihydro-γ,γ-caroten-l-ol
Rhodopinol a.k.a. Warmingol 13-cis-1,2-Dihydro-γ,γ-carotene-1,20-diol
Saproxanthin 3',4'-Didehydro-1',2'-dihydro-β,γ-carotene-3,1'-diol
Zeaxanthin
Glycosides
Oscillaxanthin 2,2'-Bis(β-L-rhamnopyranosyloxy)-3,4,3',4'-tetradehydro-1,2,1',2'-
tetrahydro-γ,γ-carotene-1,1'-diol
Phleixanthophyll 1'-(β-D-Glucopyranosyloxy)-3',4'-didehydro-1',2'-dihydro-β,γ-caroten-2'-
ol
Ethers
Rhodovibrin 1'-Methoxy-3',4'-didehydro-1,2,1',2'-tetrahydro-γ,γ-caroten-1-ol
Spheroidene 1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-γ,γ-carotene
Epoxides
Diadinoxanthin 5,6-Epoxy-7',8'-didehydro-5,6-dihydro—carotene-3,3-diol
Luteoxanthin 5,6: 5',8'-Diepoxy-5,6,5',8'-tetrahydro-β,β-carotene-3,3'-diol
Mutatoxanthin
Citroxanthin
Zeaxanthin furanoxide 5,8-Epoxy-5,8-dihydro-β,β-carotene-3,3'-diol
Neochrome 5',8'-Epoxy-6,7-didehydro-5,6,5',8'-tetrahydro-β,β-carotene-3,5,3'-triol
Foliachrome
Trollichrome
Vaucheriaxanthin 5',6'-Epoxy-6,7-didehydro-5,6,5',6'-tetrahydro-β,β-carotene-3,5,19,3'-
tetrol
Aldehydes
Rhodopinal
Warmingone 13-cis-1-Hydroxy-1,2-dihydro-γ,γ-caroten-20-al
Torularhodinaldehyde 3',4'-Didehydro-β,γ-caroten-16'-al
Acids and acid esters
Torularhodin 3',4'-Didehydro-β,γ-caroten-16'-oic acid
Torularhodin methyl ester Methyl 3',4'-didehydro-β,γ-caroten-16'-oate
Ketones
Astacene
Astaxanthin
Canthaxanthin[61] a.k.a. Aphanicin, Chlorellaxanthin β,β-Carotene-4,4'-dione
Capsanthin (3R,3'S,5'R)-3,3'-Dihydroxy-β,κ-caroten-6'-one
Capsorubin (3S,5R,3'S,5'R)-3,3'-Dihydroxy-κ,κ-carotene-6,6'-dione
Cryptocapsin (3'R,5'R)-3'-Hydroxy-β,κ-caroten-6'-one
2,2'-Diketospirilloxanthin 1,1'-Dimethoxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-γ,γ-
carotene-2,2'-dione
 Echinenone β,β-Caroten-4-one
3'-Hydroxyechinenone
Flexixanthin 3,1'-Dihydroxy-3',4'-didehydro-1',2'-dihydro-β,γ-caroten-4-one
3-OH-Canthaxanthin a.k.a. Adonirubin a.k.a. Phoenicoxanthin 3-Hydroxy-β,β-carotene-
4,4'-dione
Hydroxyspheriodenone 1'-Hydroxy-1-methoxy-3,4-didehydro-1,2,1',2',7',8'-hexahydro-
γ,γ-caroten-2-one
Okenone 1'-Methoxy-1',2'-dihydro-c,γ-caroten-4'-one
Pectenolone 3,3'-Dihydroxy-7',8'-didehydro-β,β-caroten-4-one
Phoeniconone a.k.a. Dehydroadonirubin 3-Hydroxy-2,3-didehydro-β,β-carotene-4,4'-
dione
Phoenicopterone β,ε-caroten-4-one
Rubixanthone 3-Hydroxy-β,γ-caroten-4'-one
Siphonaxanthin 3,19,3'-Trihydroxy-7,8-dihydro-β,ε-caroten-8-one
Esters of alcohols
Astacein 3,3'-Bispalmitoyloxy-2,3,2',3'-tetradehydro-β,β-carotene-4,4'-dione or 3,3'-
dihydroxy-2,3,2',3'-tetradehydro-β,β-carotene-4,4'-dione dipalmitate
Fucoxanthin 3'-Acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-
β,β-caroten-8-one
Isofucoxanthin 3'-Acetoxy-3,5,5'-trihydroxy-6',7'-didehydro-5,8,5',6'-tetrahydro-β,β-
caroten-8-one
Physalien
Siphonein 3,3'-Dihydroxy-19-lauroyloxy-7,8-dihydro-β,ε-caroten-8-one or 3,19,3'-
trihydroxy-7,8-dihydro-β,ε-caroten-8-one 19-laurate
Apocarotenoids
β-Apo-2'-carotenal 3',4'-Didehydro-2'-apo-b-caroten-2'-al
Apo-2-lycopenal
Apo-6'-lycopenal 6'-Apo-y-caroten-6'-al
Azafrinaldehyde 5,6-Dihydroxy-5,6-dihydro-10'-apo-β-caroten-10'-al
Bixin 6'-Methyl hydrogen 9'-cis-6,6'-diapocarotene-6,6'-dioate
Citranaxanthin 5',6'-Dihydro-5'-apo-β-caroten-6'-one or 5',6'-dihydro-5'-apo-18'-nor-β-
caroten-6'-one or 6'-methyl-6'-apo-β-caroten-6'-one
Crocetin 8,8'-Diapo-8,8'-carotenedioic acid
Crocetinsemialdehyde 8'-Oxo-8,8'-diapo-8-carotenoic acid
Crocin Digentiobiosyl 8,8'-diapo-8,8'-carotenedioate
Hopkinsiaxanthin 3-Hydroxy-7,8-didehydro-7',8'-dihydro-7'-apo-b-carotene-4,8'-dione or
3-hydroxy-8'-methyl-7,8-didehydro-8'-apo-b-carotene-4,8'-dione
Methyl apo-6'-lycopenoate Methyl 6'-apo-y-caroten-6'-oate
Paracentrone 3,5-Dihydroxy-6,7-didehydro-5,6,7',8'-tetrahydro-7'-apo-b-caroten-8'-one or
3,5-dihydroxy-8'-methyl-6,7-didehydro-5,6-dihydro-8'-apo-b-caroten-8'-one
Sintaxanthin 7',8'-Dihydro-7'-apo-b-caroten-8'-one or 8'-methyl-8'-apo-b-caroten-8'-one
Nor- and seco-carotenoids
Actinioerythrin 3,3'-Bisacyloxy-2,2'-dinor-b,b-carotene-4,4'-dione
β-Carotenone 5,6:5',6'-Diseco-b,b-carotene-5,6,5',6'-tetrone
Peridinin 3'-Acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,5',6'-tetrahydro-
12',13',20'-trinor-b,b-caroten-19,11-olide
 Pyrrhoxanthininol 5,6-epoxy-3,3'-dihydroxy-7',8'-didehydro-5,6-dihydro-12',13',20'-trinor-
b,b-caroten-19,11-olide
Semi-α-carotenone 5,6-Seco-b,e-carotene-5,6-dione
Semi-β-carotenone 5,6-seco-b,b-carotene-5,6-dione or 5',6'-seco-b,b-carotene-5',6'-
dione
Triphasiaxanthin 3-Hydroxysemi-b-carotenone 3'-Hydroxy-5,6-seco-b,b-carotene-5,6-
dione or 3-hydroxy-5',6'-seco-b,b-carotene-5',6'-dione
Retro-carotenoids and retro-apo-carotenoids
Eschscholtzxanthin 4',5'-Didehydro-4,5'-retro-b,b-carotene-3,3'-diol
Eschscholtzxanthone 3'-Hydroxy-4',5'-didehydro-4,5'-retro-b,b-caroten-3-one
Rhodoxanthin 4',5'-Didehydro-4,5'-retro-b,b-carotene-3,3'-dione
Tangeraxanthin 3-Hydroxy-5'-methyl-4,5'-retro-5'-apo-b-caroten-5'-one or 3-hydroxy-4,5'-
retro-5'-apo-b-caroten-5'-one
Higher carotenoids
Nonaprenoxanthin 2-(4-Hydroxy-3-methyl-2-butenyl)-7',8',11',12'-tetrahydro-e,y-carotene
Decaprenoxanthin 2,2'-Bis(4-hydroxy-3-methyl-2-butenyl)-e,e-carotene
C.p. 450 2-[4-Hydroxy-3-(hydroxymethyl)-2-butenyl]-2'-(3-methyl-2-butenyl)-b,b-carotene
C.p. 473 2'-(4-Hydroxy-3-methyl-2-butenyl)-2-(3-methyl-2-butenyl)-3',4'-didehydro-l',2'-
dihydro-β,γ-caroten-1'-ol
Bacterioruberin 2,2'-Bis(3-hydroxy-3-methylbutyl)-3,4,3',4'-tetradehydro-1,2,1',2'-
tetrahydro-γ,γ-carotene-1,1'-diol

See also
List of phytochemicals in food
CRT (genetics), gene cluster responsible for the biosynthesis of carotenoids
E number#E100–E199 (colours)
Phytochemistry

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External links
Carotenoid Terpenoids (http://www.benbest.com/nutrceut/phytochemicals.html#carotenoids)
Carotenoids as Flavor and Fragrance Precursors (http://leffingwell.com/caroten.htm)
Carotenoid gene in aphids (https://www.nsf.gov/news/news_summ.jsp?cntn_id=116842&W
T.mc_id=USNSF_52&WT.mc_ev=click)
 International Carotenoid Society (http://www.carotenoidsociety.org/)
Carotenoids (https://meshb.nlm.nih.gov/record/ui?name=Carotenoids) at the US National
Library of Medicine Medical Subject Headings (MeSH)

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