(-)-Fenchone
Basic information
- CAS
1195-79-5- Standard SMILES
CC1(C)C(=O)[C@]2(C)CC[C@H]1C2- InChIKey
LHXDLQBQYFFVNW-OIBJUYFYSA-N- Molecular formula
- C10H16O
- Average molar mass
- 152.23 g/mol
- Monoisotopic mass
- 152.12011513
Overview
(1R,4S)-fenchone is a fenchone that has (1R,4S)-stereochemistry. It is a constituent of the essential oils obtained from fennel. It has a role as a plant metabolite. It is an enantiomer of a (1S,4R)-fenchone.
Names & identifiers
- Preferred name
- (-)-Fenchone
- IUPAC
- (1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
- English name
- Fenchone
- Molecular formula
- C10H16O
- Molecular weight
- 152.23
Names & synonyms
(-)-Fenchone7787-20-4L-Fenchone(1R)-(-)-Fenchonel-alpha-Fenchone(1R,4S)-fenchone(1R)-fenchone(1R,4S)-fenchan-2-oneFenchone, (-)-K6G5Y2Y3Q2FEMA NO. 4519(4R)-2,2,4-trimethylbicyclo(2.2.1)heptan-3-one
Show more names
NEFenchonNSC 8896FENCHONENSC 122687DL-fenchone3,3-dimethyl-DELTA-FENCHONEFENCHON TECHN.1,3,3-Trimethylnorcamphor
(1R,4S)-(-)-Fenchonefenchone, (1R)-isomerRefChem:1049105EINECS 232-107-5( -)-Fenchone(-)-1,3,3-Trimethyl-2-norbornanone232-107-5(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
Database identifiers
- CAS
1195-79-5、7787-20-4- PubChem CID
- 82229
- DTXSID
DTXSID30884431- ChEMBL
CHEMBL2269327- ChEBI
CHEBI:36612- UNII
- 4Q6W8568TG、K6G5Y2Y3Q2
- EC Number
- 232-107-5
- Nikkaji
- J209.323E
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 217
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
FragrancesFragrance Ingredient (l-Fenchone) -> IFRA transparency List
LogP3.17
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.941-0.946
Solubility
Practically insoluble to insoluble
Soluble (in ethanol)
Boiling Point192-194 °CC
Refractive Index1.461-1.465
Physical DescriptionClear colorless to pale yellow liquid, Camphor herbal earthy woody aroma
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 84.5% (284 of 336) of all reports.
Warning
H226 (14%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 336 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
REACH registered substance: 1,3,3-trimethylnorbornan-2-one (EC: 232-107-5)
Bicyclo2.2.1heptan-2-one, 1,3,3-trimethyl-, (1R,4S)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesFlam. Liq. 3 (14%)
Safety data
- tsca
- TSCA listed
- Signal word
- Warning
- Symbol(GHS)
- GHS02
- Hazard statements
- H226
- REACH Registrations
- Inactive
Chemistry & industry
Uses & manufacturing
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationBicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1R,4S)-: ACTIVE
Applications
UsesFenchone has a wide range of uses, such as:1. constituent of absinthe and the essential oil of fennel2. used to repel insects3. used as flavor in candy and baked goods, as well as alcoholic and non-alcoholic beverages4. used for soaps, detergents, perfumes, lotions
UsesFenchone is a monoterpene with anti-inflammatory and antimicrobial properties. It also inhibits β-secretase (BACE1), a drug target for Alzheimer''s disease.
Additional notes
DefinitionChEBI: Fenchone is a carbobicyclic compound that is fenchane in which the hydrogens at position 2 are replaced by an oxo group. It is a component of essential oil from fennel (Foeniculum vulgare). It has a role as a plant metabolite. It is a fenchane monoterpenoid, a cyclic terpene ketone and a carbobicyclic compound.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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