Basic information
- CAS
23696-85-7- Standard SMILES
C/C=C/C(=O)C1=C(C)C=CCC1(C)C- InChIKey
POIARNZEYGURDG-FNORWQNLSA-N- Molecular formula
- C13H18O
- Average molar mass
- 190.28 g/mol
- Monoisotopic mass
- 190.1357652
Overview
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 volatile oil component, a fragrance and a plant metabolite. It is a cyclic monoterpene ketone, an apo carotenoid monoterpenoid and an enone.
Names & identifiers
- Preferred name
- beta-Damascenone
- IUPAC
- (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
- English name
- beta-Damascenone
- Molecular formula
- C13H18O
- Molecular weight
- 190.28
Names & synonyms
beta-Damascenone23726-93-4trans-beta-Damascenonetrans-damascenone(E)-beta-damascenoneFEMA No. 3420(E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneU66V25TBO04-(2,6,6-Trimethylcyclohexa-1,3-dienyl)but-2-en-4-oneCHEBI:67251DTXSID908852421-[2,6,6-Trimethyl-1,3-cyclohexadien-1-yl]-2E-buten-1-one
Show more names
(E)-β-DamascenoneB-DAMASCENONEtrans-β-Damascenone1-(2,6,6-TRIMETHYLCYCLOHEXA-1,3-DIENYL)-2-BUTEN-1-ONE(2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-oneDoricenonDoricenone
1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2E-buten-1-oneRefChem:567817DTXCID4021397245-833-2245-844-223696-85-7(E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one.beta.-Damascenone
Database identifiers
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
- Formal charge
- 0
- Complexity
- 327
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C40 isoprenoids (tetraterpenes) [PR0107]
SpringerMaterials PropertiesDielectric constant
FragrancesFragrance Ingredient (1-(2,6,6-Trimethylcyclohexa-1,3-dienyl)-2-buten-1-one) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.945-0.952 (20 °C)
Flavoring AgentsEU Flavoring substances
Solubility1 ml in 10 ml 95% alcohol (in ethanol)
Boiling Point
274.00 to 276.00 °C. @ 760.00 mm Hg
60 °C
Refractive Index1.508-1.514
Physical Description
CBI
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (69.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P272, P273, P280, P302+P352, P321, P332+P317, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1954 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H315 (33.9%): Causes skin irritation [Warning Skin corrosion/irritation]
Hazard information
Regulatory Information
Chemical: 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-
Regulation (EC) No 1831/2003 (amended)
2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: (E)-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one (EC: 245-844-2)
2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Damascones: Human health tier II assessment
Hazard Classes and Categories
Skin Irrit. 2 (69.9%)
Skin Irrit. 2 (33.9%)
Skin sensitisation - category 1
Safety data
- tsca
- TSCA listed
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Uses & manufacturing
U.S. Production2023: <50,000 lb
Consumer UsesFragrance
Household ProductsInformation on 10 consumer products that contain Rose Ketone-4 in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information
2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-: ACTIVE
2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (2E)-: ACTIVE
Applications
UsesA terpenic ketone; odorant in fruits, vegetables, honey, wine and beer
Upstream & downstream products
Upstream raw materials
Related reactions
16 records
Compound notes
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