(E)-β-Damascenone

(E)-β-Damascenone
Compound Structure:
Synonyms: Damascenone; beta-Damascenone; trans-beta-Damascenone;trans-damascenone;2-BUTEN-1-ONE, 1-(2,6,6-TRIMETHYL-1,3-CYCLOHEXADIEN-1-YL)-;1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one;(E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
Compound ID: NMPC-048
PubChem ID:

5366074
Molecular Formula: C13H18O
Canonical SMILES: CC=CC(=O)C1=C(C=CCC1(C)C)C
InChIKey: POIARNZEYGURDG-FNORWQNLSA-N
About the compound:

Beta-damascenone is a cyclic monoterpene ketone, specifically 2,6,6-trimethylcyclohexa-1,3-diene substituted at position 1 by a crotonoyl group. This compound serves multiple roles as a fragrance, a volatile oil component, and a plant metabolite. It falls into the categories of an enone, an apo carotenoid monoterpenoid, and a cyclic monoterpene ketone. Damascenone, of which beta-damascenone is a type, is a natural product found in various organisms, including Vitis rotundifolia and Vitis labrusca. Damascenones are part of a group of closely related chemical compounds found in various essential oils. They are categorized as rose ketones, alongside damascones and ionones. Beta-damascenone is a key contributor to the aroma of roses, even though it is present in very low concentrations. This compound plays a crucial role in perfumery as an essential fragrance chemical. Damascenones are derived from the degradation of carotenoids. Notably, (E)-β-damascenone was identified as a primary odorant in Kentucky bourbon in 2008, demonstrating its significance in providing aroma to various products.https://en.wikipedia.org/wiki/Damascenone

GHS Hazard Statements

• H315 (69.8%): Causes skin irritation [Warning Skin corrosion/irritation]

• H317 (99.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]

• H411 (99.79%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
Properties:

Chemical and Physical Properties

 

Property Name

Property Value

Molecular Weight

190.28 g/mol

XLogP3-AA

3.2

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

2

Exact Mass

190.135765193 g/mol

Monoisotopic Mass

190.135765193 g/mol

Topological Polar Surface Area

17.1Ų

Heavy Atom Count

14

Formal Charge

0

Complexity

327

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

1

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

pale yellow to yellow liquid with a floral, fruity odour

Boiling Point

274.00 to 276.00 °C. @ 760.00 mm Hg

Density

0.945-0.952 (20°)

Solubility 

1 ml in 10 ml 95% alcohol (in ethanol)

Source: PubChem
Source Species: Crateva adansonii
Ehretia cymosa
Vitex doniana
Hirsute Palisota
Tecoma stans
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