1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one

• ChemBase ID: 126859
• Molecular Formular: C13H18O
• Molecular Mass: 190.28142
• Monoisotopic Mass: 190.1357652
• SMILES: O=C(C1=C(C=CCC1(C)C)C)/C=C/C
• Canonical SMILES: C/C=C/C(=O)C1=C(C)C=CCC1(C)C
• InChI: InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3
• InChIKey: POIARNZEYGURDG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one; (2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
• IUPAC Traditional name: 1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one; damascenone
• Synonyms: Damascenone; (2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; trans-2,6,6-Trimethyl-1-crotonylcyclohexa-1,3-diene; Doricenone; β-Damascenone, 90%DISCONTINUED, UNSTABLE; Damascenone; 大马酮

Database IDs

• CAS Number: 23726-93-4; 23696-85-7
• MDL Number: MFCD00101024
• PubChem SID: 162221186; 24901692
• PubChem CID: 5366074
• CHEBI ID: 67251
• Chemspider ID: 4517997
• FEMA ID: 3420
• Wikipedia Title: Damascenone
• Flavis Number: 7.108

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.6816037
• LogD (pH = 7.4): 3.6816037
• Log P: 3.6816037
• Molar Refractivity: 63.0164 cm^3
• Polarizability: 23.3284 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol (950C)
• Apperance: Pale Yellow to Yellow Liquid; yellow liquid
• Melting Point: 116-118°C
• Flash Point: 16 °C; 60.8 °F
• Density: 0.800 g/mL at 25 °C; 0.800-0.830 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.350-1.380(lit.)
• Organoleptic: apple; woody; herbaceous; citrus; nutty; rose; smoky; wine-like

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1170
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-43
• Safety Statements: 16-36/37
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H317
• GHS Precautionary statements: P210-P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Concentration: 1.1-1.3 wt. % (190 proof ethanol)
• Grade: Halal; Kosher; natural
• Empirical Formula (Hill Notation): C13H18O

DETAILS

Sigma Aldrich - W342017

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.
Packaging
1 kg in glass bottle
1 sample in glass bottle
25, 100 g in glass bottle

Toronto Research Chemicals - D134500

A terpenic ketone; odorant in fruits, vegetables, honey, wine and beer.

REFERENCES

• Sen, A., et al.: J. Agric. Food Chem., 39, 757 (1991)
• Chevance, F., et al.: J. Agric. Food Chem., 50, 3818 (1991)
• Daniel, M.A., et al.: J. Agric. Food Chem., 52, 8127 (2004)