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References (1) View in SciFinder n

Ambergris revisited . Isolation of volatile constituents ; identification and synthesis of

ambra - aldehyde C14H22O

By: Jegou, Elise; Polonsky, Judith; Lederer, Edgar; Schulte-Elte, Karl Heinz; Egger, Bernard; Ohloff, Guenther
Nouveau Journal de Chimie (1977), 1(6), 529-31 | Language: English, Database: CAplus

Preparative thin-layer chromatog. of steam distilled Et2O-soluble fraction of ambergris (an intestinal concretion of the sperm whale)
separated 5 compounds which were identified as dihydro-γ-ionone (I) [13720-12-2], a hemiketal II [13017-23-7], an unsaturated
oxide III [10281-45-5], α-ambrinol [77286-35-2], and a new aldehyde with marine odor ambra- aldehyde (IV) [65716-62-3]. Structure
of IV was further confirmed by its synthesis.

Keywords: ambergris sperm whale ambra aldehyde

OH
Me
C H2 O
Me
X

R CCH 2 CH2 I , R=Me, X=O

H
Me Me I V , R=CHO, X=CH Me
2 Me II

O
Me
III

Substances (6) Reactions (0) Cited By (11)

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Substances (6) View in SciFinder n

13720-12-2 Key Physical Properties Value Condition

Molecular Weight 194.31 -

Melting Point (Experimental) 111-112 °C -

Boiling Point (Predicted) 257.9±9.0 °C Press: 760 Torr

Density (Predicted) 0.89±0.1 g/cm3 Temp: 20 °C; Press: 760 Torr

C13 H22 O Experimental Properties | Spectra

Dihydro-γ-ionone

76 64 6
References Reactions Suppliers

77286-35-2 Key Physical Properties Value Condition

Molecular Weight 194.31 -

Boiling Point (Predicted) 280.1±9.0 °C Press: 760 Torr

Density (Predicted) 0.98±0.1 g/cm3 Temp: 20 °C; Press: 760 Torr

Relative stereochemistry shown pKa (Predicted) 15.13±0.40 Most Acidic Temp: 25 °C

Spectra
C13 H22 O
rel-(2R,4aR)-1,2,3,4,4a,5,6,7-Octahydro-2,5,5-
trimethyl-2-naphthalenol

50 20 0
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10281-45-5 Key Physical Properties Value Condition

Molecular Weight 248.40 -

Boiling Point (Predicted) 311.5±9.0 °C Press: 760 Torr

Density (Predicted) 0.945±0.06 g/cm3 Temp: 20 °C; Press: 760 Torr

Absolute stereochemistry shown, Spectra

Rotation (-)

C17 H28 O
(4aR,6aS,10aS,10b R)-4a,5,6,6a,7,8,9,10,10a,
10b-Decahydro-4a,7,7,10a-tetramethyl-1H-
naphtho[2,1- b ]pyran

14 5 0
References Reactions Suppliers

13017-23-7 Key Physical Properties Value Condition

Molecular Weight 266.42 -

Melting Point 196 °C -

(Experimental)

Boiling Point (Predicted) 310.1±10.0 °C Press: 760 Torr

Absolute stereochemistry shown
Density (Predicted) 1.000±0.06 Temp: 20 °C; Press: 760 Torr
g/cm3
C17 H30 O2
(4aR,6aS,10aS,10b R)-Dodecahydro-4a,7,7,10a- pKa (Predicted) 13.20±0.70 Most Acidic Temp: 25 °C
tetramethyl-1H-naphtho[2,1- b ]pyran-3-ol
Experimental Properties | Spectra
11 17 0
References Reactions Suppliers

65716-62-3 Key Physical Properties Value Condition

Molecular Weight 206.32 -

Boiling Point (Predicted) 287.1±9.0 °C Press: 760 Torr

Density (Predicted) 0.89±0.1 g/cm3 Temp: 20 °C; Press: 760 Torr

Absolute stereochemistry shown,

Rotation (+)

C14 H22 O
(1S)-2,2-Dimethyl-α,6-bis(methylene)
cyclohexanebutanal

9 22 0
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66084-43-3 Key Physical Properties Value Condition

Molecular Weight 362.53 -

Boiling Point (Predicted) 475.9±38.0 °C Press: 760 Torr

Density (Predicted) 1.10±0.1 g/cm3 Temp: 20 °C; Press: 760 Torr

Absolute stereochemistry shown pKa (Predicted) 10.46±0.40 Most Acidic Temp: 25 °C

Double bond geometry unknown

C20 H30 N 2O2S

Benzenesulfonic acid, 4-methyl-, [3-(2,2-
dimethyl-6-methylenecyclohexyl)-1-
methylpropylidene]hydrazide, ( S)-

1 0 0
Reference Reactions Suppliers

Copyright © 2022 American Chemical Society (ACS). All Rights Reserved.

Internal use only. Redistribution is subject to the terms of your SciFinderⁿ License Agreement and CAS information Use Policies.