Damascenone

HCID 62775
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Basic information

CAS
23696-85-7
Standard SMILES
CC=CC(=O)C1=C(C)C=CCC1(C)C
InChIKey
POIARNZEYGURDG-UHFFFAOYSA-N
Molecular formula
C13H18O
Average molar mass
190.28 g/mol
Monoisotopic mass
190.1357652

Overview

(E/Z)-damascenone has been reported in Centaurea armena, Iris × germanica, and other organisms with data available.

Names & identifiers

Preferred name
Damascenone
IUPAC
1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
English name
Damascenone
Molecular formula
C13H18O
Molecular weight
190.28

Names & synonyms

DTXSID6041397DTXCID80196511RefChem:919620Damascenoneb-damascenone2,6,6-Trimethyl-1-crotonyl-1,3-cyclohexadiene1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-; 1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; 1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-buten-1-one; 1-Crotonoyl-2,6,6-trimethyl-1,3-cyclohexadiene; 2,6,6-Trimethyl-1-(2-butenoyl)-1,3-cyclohexadiene; 2,6,6-Trimethyl-1-crotonyl-1,3-cyclohexadieneSCHEMBL164856orb1222483POIARNZEYGURDG-UHFFFAOYSA-N1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; 1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-buten-1-one; 1-Crotonoyl-2,6,6-trimethyl-1,3-cyclohexadiene; 2,6,6-Trimethyl-1-(2-butenoyl)-1,3-cyclohexadiene
Show more names
β-Damascenone2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-DAMASCENONE TOTALFEMA 34201-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-Buten-1-one4-(2,6,6-Trimethyl cyclohexa-1,3-dienyl)but-2-en-4-one(E)-1-(2,6,6-triMethylcyclohexa-1,3-dien-1-yl)but-2-en-1-oneDamasioneDAMASCENONTrimethyl cyclohexadienyl butenone
s6431AKOS028110970DB-336645NS00075807(E)-beta-Damascenone 1000 microg/mL in Acetonitrile2,6,6-trimethyl-1-(but-2-enoyl)-cyclohexa-1,3-dien1-(2,6,6-trimethylcyclohexa-1,3-dienyl) but-2-en-1one1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)-2-buten-1-one

Database identifiers

CAS
23696-85-7
PubChem CID
62775
DTXSID
DTXSID6041397

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
14

Physicochemical properties

Boiling point
275.6 · 275.6±10.0 °C(Predicted)
Density
0.8 · 0.800-0.830 g/mL at 25 °C (lit.)
refractive index
1.35 · 1.350-1.380
FEMA
3420 · 3420 | 1-(2,6,6-TRIMETHYLCYCLOHEXA-1,3-DIENYL)-2-BUTEN-1-ONE
FLAVIS Number
7.108 · 07.108 | beta-Damascenone
Flash point
62 °F · 62°F

Safety & regulation

Safety data

wgk
3
tsca
TSCA listed
ridadr
UN 1170
hs_code
33021090
risk_code
11-43
Signal word
Danger

Chemistry & industry

Uses & manufacturing

Use ClassificationFlavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications · 3 items

OccurrenceReported found in raspberry oil, Burley tobacco, apple, lemon balm, summer savory, anise, hyssop, apple juice, cooked apple, apricot, sweet and sour cherry, black currant berries, fresh blackberry, strawberry jam, hop oil rum, white wine, red wine, black tea, tomato, rye bread, blue cheese, cow, goat and sheep milk, hop oil, beer, cognac, rum, whiskies, scotch, cider, grape wines, coffee, tea, popcorn, oatmeal, soybean, plum, prune, beans, starfruit, mango, tamarind, dill seed, corn oil, okra, cape gooseberry, anise hyssop and Roman chamomile oil.

UsesDamascenone 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.

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

Preparation methods

PreparationBy treating the corresponding ethyl safranate with allyl lithium, followed by catalytic isomerization of the reaction product; also from the oxirane derivative of β-damascone by an acid-catalyzed reaction.

Upstream & downstream products

Downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Beta-damascenone is a cyclic monoterpene ketone that is 2,6,6-trimethylcyclohexa-1,3-diene substituted at position 1 by a crotonoyl group. It has a role as a fragrance, a volatile oil component and a plant metabolite. It is an enone, an apo carotenoid monoterpenoid and a cyclic monoterpene ketone.

Related reactions

4 records
New reaction record

Compound notes

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