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491-09-8

491-09-8 Structure

491-09-8 Structure
IdentificationBack Directory
[Name]

3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one
[CAS]

491-09-8
[Synonyms]

piperitenone
1,4(8)-p-Menthadien-3-one
p-Mentha-1,4(8)-diene-3-one
PARA-MENTH-1,4(8)-DIEN-3-ONE
PARA-MENTHA-1,4(8)-DIEN-3-ONE
6-Isopropylidene-3-methyl-2-cyclohexen-1-one
3-Methyl-6-(propan-2-ylidene)cyclohex-2-enone
3-Methyl-6-isopropylidene-2-cyclohexene-1-one
3-Methyl-6-propan-2-ylidenecyclohex-2-en-1-one
3-methyl-6-(1-methylethylidene)-2-cyclohexen-1-on
3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one
3-Methyl-6-(1-methylethylidene)-2-cyclohexene-1-one
2-Cyclohexen-1-one, 3-methyl-6-(1-methylethylidene)-
Benzo[b]thiophene-2-carboxylicacid,3-chloro-5,8-dimethoxy-,methylester
[EINECS(EC#)]

207-729-5
[Molecular Formula]

C10H14O
[MOL File]

491-09-8.mol
[Molecular Weight]

150.218
Chemical PropertiesBack Directory
[Melting point ]

184-184.5 °C
[Boiling point ]

231.78°C (rough estimate)
[density ]

0.9774
[FEMA ]

3560 | P-MENTHA-1,4(8)-DIEN-3-ONE
[refractive index ]

1.5294 (estimate)
[storage temp. ]

2-8°C
[solubility ]

DMF: miscible; DMSO: miscible; Ethanol: miscible
[Odor]

at 10.00 % in dipropylene glycol. sharp minty phenolic
[Odor Type]

minty
[JECFA Number]

757
[LogP]

2.87
[EPA Substance Registry System]

2-Cyclohexen-1-one, 3-methyl-6-(1-methylethylidene)- (491-09-8)
Hazard InformationBack Directory
[Description]

Piperitenone 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 .
[Chemical Properties]

p-Mentha-1,4(8)-dien-3-one has a powerful sharp, herbal minty, phenolic odor.
[Occurrence]

Reported 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.
[Definition]

ChEBI: Piperitenone is a p-menthadien-3-one.
[Aroma threshold values]

Detection; 680 ppb
[Synthesis Reference(s)]

The Journal of Organic Chemistry, 52, p. 1505, 1987 DOI: 10.1021/jo00384a023
[References]

[1] CARLTON E. TURNER  Edward G B  Mahmoud A Elsohly. Constituents of Cannabis sativa L. XVII. A Review of the Natural Constituents[J]. Journal of Natural Products , 1980, 43 2: 169-234. DOI: 10.1021/np50008a001
[2] TAHSEEN IQBAL. Antioxidant Activity and Volatile and Phenolic Profiles of Essential Oil and Different Extracts of Wild Mint (Mentha longifolia) from the Pakistani Flora.[J]. Journal of Analytical Methods in Chemistry, 2013, 2013: 536490. DOI: 10.1155/2013/536490
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