CAS 491-09-8 Piperitenone (HCID 381152)

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Basic information

CAS: 491-09-8
Standard SMILES: CC1=CC(=O)C(=C(C)C)CC1
InChIKey: HKZQJZIFODOLFR-UHFFFAOYSA-N
Molecular formula: C10H14O
Average molar mass: 150.22 g/mol
Monoisotopic mass: 150.10446507

Names & identifiers

Preferred name: Piperitenone
IUPAC: 3-methyl-6-propan-2-ylidenecyclohex-2-en-1-one
English name: 3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one
Molecular formula: C10H14O
Molecular weight: 150.22

Names & synonyms

Piperitenone491-09-83-TerpinolenonePulespenonep-Mentha-1,4(8)-dien-3-one2-CYCLOHEXEN-1-ONE, 3-METHYL-6-(1-METHYLETHYLIDENE)-3-Methyl-6-(1-methylethylidene)cyclohex-2-en-1-oneFEMA No. 3560IKR841W74D1-Methyl-4-isopropylidene-1-cyclohexen-3-oneNSC-667470CHEBI:17304

Show more names

1,4(8)-p-Menthadien-3-onep-Mentha-1,4(8)-diene-3-onePARA-MENTH-1,4(8)-DIEN-3-ONEPARA-MENTHA-1,4(8)-DIEN-3-ONE6-Isopropylidene-3-methyl-2-cyclohexen-1-one3-Methyl-6-isopropylidene-2-cyclohexene-1-one

DTXSID10883402RefChem:863607DTXCID001022936207-729-53-Methyl-6-(propan-2-ylidene)cyclohex-2-enone3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one3-methyl-6-propan-2-ylidenecyclohex-2-en-1-one3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one

Database identifiers

CAS: 491-09-8
PubChem CID: 381152
DTXSID: DTXSID10883402
ChEMBL: CHEMBL54161
ChEBI: CHEBI:17304
UNII: IKR841W74D
EC Number: 207-729-5
Nikkaji: J6.050J

Properties

Computed structural properties

XLogP: 2.2
Topological polar surface area: 17.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 0
Heavy atoms: 11
Formal charge: 0
Complexity: 240

Experimental & physicochemical properties

Density0.976-0.983

Solubility · 2 items

insoluble in water; soluble in oils

miscible (in ethanol)

Boiling Point · 2 items

106.00 to 107.00 °C. @ 10.00 mm Hg

233 °C

Refractive Index1.472-1.478

Physical DescriptionYellow to amber oily liquid, powerful sharp, minty, phenolic odour

Kovats Retention Index · 3 items

1340；1315；1316；1310；1304；1312；1317；1286；1316；1316；1340；1320；1324；1324；1324；1315

1349；1343；1343；1344；1339；1309；1347；1343；1343；1347；1343；1338；1342；1340；1329；1329；1339；1348；1297；1339

1909；1949；1948；1949；1949；1949；1918；1949；1930；1949；1949；1949；1949；1956；1949；1949

Physicochemical properties

Melting point: 184 · 184-184.5 °C
Boiling point: 231.78 °C · 231.78°C (rough estimate)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Warning

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H412 (50%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 2 reports by companies.；There is 1 notification provided by 1 of 2 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 3 items

Chemical: 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethylidene)-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Cyclohexen-1-one, 3-methyl-6-(1-methylethylidene)-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia

Hazard Classes and CategoriesSkin Irrit. 2 (50%)；Eye Irrit. 2A (50%)；STOT SE 3 (50%)；Aquatic Chronic 3 (50%)

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm；Extracellular；Membrane

Uses & manufacturing

Use Classification · 4 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information2-Cyclohexen-1-one, 3-methyl-6-(1-methylethylidene)-: INACTIVE

Applications · 2 items

DescriptionPiperitenone is a monoterpene that has been found in various plants, including Cannabis, and has antioxidant activity. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell free assay (IC50 = 22.7 μg/ml). Piperitenone also inhibits peroxidation of linoleic acid .

OccurrenceReported present in pennyroyal, spearmint and Scotch spearmint oils, citrus peel oils and juices, black cur rants, cardamom, origanum, buchu oil, lemon balm and mastic gum fruit oil.