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W342017

Sigma-Aldrich

Damascenone

natural, 1.1-1.4 wt. % (190 proof ethanol), FG

Synonym(s):

β-Damascenone, 1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)-2-buten-1-one

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About This Item

Empirical Formula (Hill Notation):
C13H18O
CAS Number:
23696-85-7
Molecular Weight:
190.28
FEMA Number:
3420
MDL number:
MFCD00101024
UNSPSC Code:
12164502
PubChem Substance ID:
24901692
Flavis number:
7.108
NACRES:
NA.21

grade

FG
Fragrance grade
Kosher
natural

Quality Level

400

Agency

follows IFRA guidelines

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 872/2012
FDA 21 CFR 110

form

liquid

concentration

1.1-1.4 wt. % (190 proof ethanol)

color

yellow

refractive index

n20/D 1.350-1.380 (lit.)

density

0.800-0.830 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

apple; smoky; herbaceous; nutty; citrus; woody; rose; wine-like

storage temp.

2-8°C

SMILES string

C\C=C\C(=O)C1=C(C)C=CCC1(C)C

InChI

1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+

InChI key

POIARNZEYGURDG-FNORWQNLSA-N

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General description

Damascenone is a norisoprenoid ketone mainly found in red wines. It occurs naturally in tomato and grapes.

Application

Damascenone is a fragrance ingredient that can be used in shampoos, fine fragrances, decorative cosmetics, toilet soaps as well as non-cosmetic products like household cleaners and detergents.

Biochem/physiol Actions

Taste at 1-5 ppm

Other Notes

Natural occurrence: Apple juice, apricot, black currant, grape, raspberry, strawberry, cognac, rum, whiskey and scotch.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H317,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Sens. 1

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

60.8 °F - closed cup

Flash Point(C)

16 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bénédicte Pineau et al.
Journal of agricultural and food chemistry, 55(10), 4103-4108 (2007-04-24)
beta-Damascenone, a C-13 norisoprenoid compound, is usually presented as an impact odorant in red wines. Its direct contribution to their aroma was investigated. Both free beta-damascenone and beta-damascenone precursors were isolated from various French red wines and then analyzed by
Merran A Daniel et al.
Journal of agricultural and food chemistry, 52(26), 8127-8131 (2004-12-23)
Damascenone has been shown to undergo reaction with common wine components. Following the action of acid and heat alone, two bicyclic compounds, 4,9,9-trimethyl-8-methylenebicyclo[3.3.1]non-6-en-2-one (2) and 4,4,9-trimethyl-8-methylenebicyclo[3.3.1] non-6-en-2-one (3), were isolated. However, this conversion takes place only very slowly, if at
Alexandre Pons et al.
Journal of agricultural and food chemistry, 56(13), 5285-5290 (2008-06-11)
The premature aging of red Vitis vinifera L. wines is mainly associated with the formation of an intense off-flavor reminiscent of prunes. The compounds responsible for this deterioration in red wine flavor have not previously been identified. Sensory descriptive analysis
Yair Bezman et al.
Journal of agricultural and food chemistry, 53(23), 9199-9206 (2005-11-10)
The potent odorant beta-damascenone was formed directly from 9'-cis-neoxanthin in a model system by peroxyacetic acid oxidation and two-phase thermal degradation without the involvement of enzymatic activity. Beta-damascenone formation was heavily dependent on pH (optimum at 5.0) and temperature, occurring
U Pongprayoon et al.
Planta medica, 58(1), 19-21 (1992-02-01)
The crude extract (IPA) of the plant Ipomoea pes-caprae (L.) R. Br. has previously been shown to antagonize smooth muscle contractions induced by several agonists via a non-specific mechanism. Bioassay-guided fractionation of IPA resulted in isolation of the antispasmodically acting
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