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(S)-(-)-pulegone
cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (5S)-

Supplier Sponsors

Name:	(5S)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
CAS Number:	3391-90-0	3D/inchi
FDA UNII:	HL7Z89M60H
Nikkaji Web:	J598.239A
Beilstein Number:	2040703
MDL:	MFCD00142347
XlogP3-AA:	2.80 (est)
Molecular Weight:	152.23672000
Formula:	C10 H16 O
NMR Predictor:	Predict (works with chrome, Edge or firefox)

Category:flavor and fragrance agents

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:	Search
Google Books:	Search
Google Scholar: with word "volatile"	Search
Google Scholar: with word "flavor"	Search
Google Scholar: with word "odor"	Search
Perfumer and Flavorist:	Search
Google Patents:	Search
US Patents:	Search
EU Patents:	Search
Pubchem Patents:	Search
PubMed:	Search
NCBI:	Search

Physical Properties:

Appearance:	colorless clear liquid (est)
Assay:	97.00 to 100.00
Food Chemicals Codex Listed:	No
Specific Gravity:	0.93700 @ 25.00 °C.
Refractive Index:	1.48800 @ 20.00 °C.
Boiling Point:	222.00 to 223.00 °C. @ 760.00 mm Hg
Vapor Pressure:	0.093000 mmHg @ 25.00 °C. (est)
Flash Point:	185.00 °F. TCC ( 85.00 °C. )
logP (o/w):	2.556 (est)
Soluble in:
	alcohol
	water, 173.7 mg/L @ 25 °C (est)
Insoluble in:
	water

Organoleptic Properties:

Odor Description:minty

Odor and/or flavor descriptions from others (if found).

Cosmetic Information:

None found

Suppliers:

Santa Cruz Biotechnology

For experimental / research use only.

(S)-(-)-Pulegone

Sigma-Aldrich: Aldrich

For experimental / research use only.

(S)-(-)-Pulegone 98%

Safety Information:

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed. R 36/38 - Irritating to skin and eyes. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 37/39 - Wear suitable gloves and eye/face protection.

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice

Safety References:

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 57 (FGE.57)[1]: Consideration of two structurally related pulegone metabolites and one ester thereof evaluated by JECFA (55th meeting)
View page or View pdf

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :638012

National Institute of Allergy and Infectious Diseases:Data

(5S)-5-methyl-2-propan-2-ylidenecyclohexan-1-one

Chemidplus:0003391900

References:

	(5S)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	638012
Pubchem (sid):	135251209

Other Information:

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
CHEBI:	View
CHEMBL:	View
KEGG (GenomeNet):	C17623
HMDB (The Human Metabolome Database):	Search
Export Tariff Code:	2914.29.5000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Potential Blenders and core components note

For Odor

No odor group found for these

cyclopentanone
FL/FR

laevo-mono

menthyl glutarate
FL/FR

laevo-

menthyl methyl ether
FL/FR

pinocarvone
FL/FR

aldehydic

aldehydic

iso

butyraldehyde
FL/FR

anisic

estragole
FL/FR

balsamic

iso

bornyl formate
FL/FR

camphoreous

dextro-

camphor tree bark oil
FL/FR

herbal ethanone
FR

thujyl alcohol
FL/FR

citrus

ocimene quintoxide
FL/FR

earthy

3-

patchouli cyclohexanol
FR

floral

citronellal diisotridecyl acetal
FR

cyclohexyl ethyl acetate
FL/FR

cyclohexyl propanol
FR

2-

dihydrocarvyl acetate
FL/FR

2',4'-

dimethyl acetophenone
FL/FR

earthy indane
FR

floral methanol
FR

geranium oil china
FL/FR

menthadienyl formate
FR

muguet butanol
FR

ylang ylang flower oil
FL/FR

ylang ylang flower oil CO2 extract
FL/FR

ylang ylang flower oil I
FL/FR

ylang ylang flower oil II
FL/FR

ylang ylang flower oil III
FL/FR

fruity

3-

benzyl-4-heptanone
FL/FR

2-

cyclopentyl cyclopentanone
FL/FR

lilac lactone
FL/FR

green

geranium absolute
FL/FR

thiogeraniol
FL/FR

herbal

artemisyl ketone
FL/FR

barosma betulina leaf oil
FL/FR

1,4-

costmary oil (chrysanthemum balsamita)
FR

dehydroxylinalool oxide
FL/FR

iso

dihydrolavandulol
FR

(Z)-iso

dihydrolavandulyl acetate
FR

herbal undecanol
FR

hyssop oil
FL/FR

para-

menthane-3,8-diol
FL/FR

3-

octyl acetate
FL/FR

perillaldehyde
FL/FR

laevo-

perillaldehyde
FL/FR

pine hexanol
FR

D-(+)-alpha-

pinene
FL/FR

piperitone
FL/FR

rosemary absolute
FL/FR

rosemary oil morocco
FL/FR

sabinene hydrate
FL/FR

common

tansy flower oil
FR

common

tansy flower oil dutch
FR

viridiflorol
FL/FR

licorice

sweet

basil oleoresin
FL/FR

mentholic

cornmint oil
FL/FR

cornmint oil india
FL/FR

cornmint oil terpeneless
FL/FR

dextro-neo

(±)-

dextro,laevo-

laevo-

(±)-iso

laevo-

menthyl acetate
FL/FR

menthyl acetate
FL/FR

menthyl acetate racemic
FL/FR

peppermint cyclohexanone
FL/FR

dextro-

piperitone
FL/FR

iso

pulegyl acetate
FL/FR

minty

agathosma crenulata leaf oil
FL/FR

laevo-

laevo-

cis-

carvone-5,6-oxide
FL/FR

carvyl propionate
FL/FR

cyclohexanone
FR

dihydrocarveol
FL/FR

diosphenol
FL/FR

ethyl salicylate
FL/FR

bitter

fennel seed oil
FR

dextro-2,8-para-

menthadien-1-ol
FL/FR

trans-para-2,8-1-

menthadienol
FL/FR

trans-para-

menthan-2-one
FL/FR

homo

(±)-

(-)-

menthoxypropane diol
FL/FR

homo

menthyl acetate
FL/FR

2-

methyl cyclohexanone
FL/FR

methyl salicylate
FL/FR

pennyroyal oil
FL/FR

pennyroyal oil spain
FL/FR

pennyroyal oil uruguay
FL/FR

peppermint oil CO2 extract
FL/FR

peppermint oil idaho
FL/FR

peppermint oil russia
FL/FR

peppermint oil terpeneless
FL/FR

beta-

phellandrene
FL/FR

piperitenone
FL/FR

laevo-

piperitone
FL/FR

iso

propyl tiglate
FL/FR

(-)-iso

iso

pulegyl formate
FL/FR

spearmint absolute
FL/FR

spearmint oil america
FL/FR

spearmint oil terpeneless
FL/FR

tetrahydrocarvone
FL/FR

vanillin menthoxypropane diol acetal
FL/FR

wintergreen oil
FL/FR

WS-23
FL/FR

spicy

N,N-

diethyl octanamide
FR

laevo-

verbenone
FL/FR

sulfurous

buchu mercaptan
FL/FR

grapefruit menthane
FL/FR

thujonic

common

tansy oil canada
FR

tropical

beta-

cyclocitral
FL/FR

woody

para-tert-

butyl cyclohexanone
FR

patchouli ethanol
FR

patchouli hexanol
FR

cis-2-

For Flavor

No flavor group found for these

artemisyl ketone
FL/FR

cyclopentanone
FL/FR

2-

cyclopentyl cyclopentanone
FL/FR

2',4'-

dimethyl acetophenone
FL/FR

(±)-N,N-

dimethyl menthyl succinamide
FL

iso

heptyl acetate
FL

lilac lactone
FL/FR

limonen-10-yl acetate
FL

dextro-2,8-para-

menthadien-1-ol
FL/FR

cis+trans-para-1(7)8-

menthadien-2-yl acetate
FL

trans-para-2,8-1-

menthadienol
FL/FR

para-

menthane-3,8-diol
FL/FR

3-laevo-

menthoxy-2-methyl propane-1,2-diol
FL

menthyl acetate racemic
FL/FR

laevo-mono

menthyl glutarate
FL/FR

laevo-

menthyl methyl ether
FL/FR

menthyl propylene glycol carbonate
FL

2-

methyl cyclohexanone
FL/FR

beta-

phellandrene
FL/FR

(Z,Z)-

photocitral A
FL

D-(+)-alpha-

pinene
FL/FR

pinocarvone
FL/FR

piperitenone
FL/FR

piperitenone oxide
FL

iso

pulegyl formate
FL/FR

vanillin menthoxypropane diol acetal
FL/FR

laevo-

verbenone
FL/FR

viridiflorol
FL/FR

menthyl methyl lactate
FL

thujyl alcohol
FL/FR

aldehydic

aldehydic

iso

butyraldehyde
FL/FR

alliaceous

benzyl mercaptan
FL

aromatic

laevo-

perillaldehyde
FL/FR

camphoreous

camphor tree bark oil
FL/FR

coffee

2-iso

propyl pyrazine
FL

cooling

1,4-

laevo-

dextro,laevo-

menthoxypropane diol
FL/FR

homo

menthyl acetate
FL/FR

menthyl acetate
FL/FR

sabinene hydrate
FL/FR

floral

dihydrocarvyl acetate
FL/FR

geranium oil china
FL/FR

ylang ylang flower oil
FL/FR

ylang ylang flower oil CO2 extract
FL/FR

ylang ylang flower oil I
FL/FR

ylang ylang flower oil II
FL/FR

ylang ylang flower oil III
FL/FR

fruity

3-

benzyl-4-heptanone
FL/FR

green

cyclohexyl ethyl acetate
FL/FR

dihydrocarveol
FL/FR

geranium absolute
FL/FR

ocimene quintoxide
FL/FR

3-

octyl acetate
FL/FR

iso

propyl tiglate
FL/FR

thiogeraniol
FL/FR

herbal

2-

acetoxy-1,8-cineole
FL

barosma betulina leaf oil
FL/FR

hyssop oil
FL/FR

rosemary absolute
FL/FR

rosemary oil morocco
FL/FR

licorice

sweet

basil oleoresin
FL/FR

estragole
FL/FR

meaty

2-

methyl 3-(methyl thio) furan
FL

medicinal

dextro-

mentholic

cornmint oil
FL/FR

cornmint oil terpeneless
FL/FR

dextro-neo

(±)-

peppermint cyclohexanone
FL/FR

minty

agathosma crenulata leaf oil
FL/FR

laevo-

laevo-

cis-

carvone-5,6-oxide
FL/FR

carvyl propionate
FL/FR

cornmint oil india
FL/FR

diosphenol
FL/FR

ethyl salicylate
FL/FR

trans-para-

menthan-2-one
FL/FR

homo

(±)-

(±)-iso

(-)-

laevo-

menthyl acetate
FL/FR

methyl salicylate
FL/FR

pennyroyal oil
FL/FR

pennyroyal oil spain
FL/FR

pennyroyal oil uruguay
FL/FR

peppermint oil CO2 extract
FL/FR

peppermint oil idaho
FL/FR

peppermint oil russia
FL/FR

peppermint oil terpeneless
FL/FR

dextro-

piperitone
FL/FR

piperitone
FL/FR

laevo-

piperitone
FL/FR

(-)-iso

spearmint absolute
FL/FR

spearmint oil america
FL/FR

spearmint oil terpeneless
FL/FR

tetrahydrocarvone
FL/FR

wintergreen oil
FL/FR

WS-23
FL/FR

musty

3-

spicy

4-

methyl biphenyl
FL

perillaldehyde
FL/FR

sulfurous

buchu mercaptan
FL/FR

grapefruit menthane
FL/FR

tropical

beta-

cyclocitral
FL/FR

woody

iso

bornyl formate
FL/FR

dehydroxylinalool oxide
FL/FR

iso

pulegyl acetate
FL/FR

Potential Uses:

FR

Occurrence (nature, food, other):note

found in nature

Synonyms:

	cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (5S)-
	cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (S)-
(S)-(-)-p-	menth-4(8)-en-3-one
(S)-p-	menth-4(8)-en-3-one
(S)-para-	menth-4(8)-en-3-one
(S)-5-	methyl-2-(1-methyl ethylidene) cyclohexanone
(S)-5-	methyl-2-(1-methylethylidene)cyclohexanone
(5S)-5-	methyl-2-(2-propanyliden)cyclohexanon
(5S)-5-	methyl-2-(propan-2-ylidene)cyclohexanone
(5S)-5-	methyl-2-propan-2-ylidenecyclohexan-1-one
(S)-2-iso	propylidene-5-methyl cyclohexanone
(S)-2-iso	propylidene-5-methyl-cyclohexanone
(5S)-2-iso	propylidene-5-methylcyclohexanone
(S)-2-iso	propylidene-5-methylcyclohexanone
(-)-	pulegone
L-	pulegone

Articles:

PubMed:Enantiospecific effect of pulegone and pulegone-derived lactones on Myzus persicae (Sulz.) settling and feeding.

PubMed:Lactones. 21. Synthesis and odoriferous properties of lactones with the p-menthane system.

PubMed:In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone.

PubMed:An efficient procedure for the preparation of (E)-alpha-alkylidenecycloalkanones mediated by a CeCl(3) x 7H(2)O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone.

PubMed:Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone.

PubMed:Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis.

PubMed:Biosynthesis of menthofuran in Mentha x piperita: stereoselective and mechanistic studies.

PubMed:Metabolic fate of S-(-)-pulegone in rat.

Notes:

None found

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