R-PULEGONE
Synonyms. (+)-(R)-Pulegone; (+)-Pulegone; (1R)-(+)-p-Menth-4(8)-en-3-one; (R)-(+)-Pulegone; (R)-Pulegone; 1-Isopropylidene-4-methyl-2-cyclohexanone; 1-Methyl-4-isopropylidene-3-cyclohexanone; delta-4(8)-p-Menthen-3-one; 3-Methyl-6-isopropylidenecyclohexanone;  (R)-5-Methyl-2-(1-methylethylidene)cyclohexanone; Pulegon; Pulegone; D-Pulegone; (R)-(+)-p-Menth-4(8)-en-3-one; (5R)-5-Methyl-2-(1-methylethylidene)cyclohexanone;  (R)-5-Methyl-2-(1-methylethylidene)cyclohexanone; p-Menth-4(8)-en-3-one; Other RN: 90449-51-7

R-PULEGONE
 

PRODUCT IDENTIFICATION

CAS RN

 89-82-7

EINECS RN

 201-943-2

FORMULA

 C10H16O

MOLE WEIGHT

 152.23

H.S CODE

 2914.29.5000

SMILES

 C1(\C(C[C@@H](C)CC1)=O)=C(/C)C

CLASSIFICATION

 Ketone, Perfume ingredient, Monoterpene

EXTRA NOTES

 FEMA No. 2963

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

Clear to yellowish liquid with strong mint odor

MELTING POINT

  

BOILING POINT

  

DENSITY

0.932 - 0.938

SOLUBILITY IN WATER

Insoluble
SOLVENT SOLUBILITY Miscible with ethanol, chloroform, Ether

VAPOR DENSITY

5.3

VAPOR PRESSURE

 

AUTOIGNITION TEMP

  
pH

 

REFRACTIVE INDEX

1.485 - 1.488

FLASH POINT

82 C

 
STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents
DECOMPOSITION PRODUCTS

Carbon oxides.
POLYMERIZATION

 

NFPA RATINGS

Health Hazard: 1, Fire: 2, Reactivity Hazard: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Pulegone

PubChem Compound Summary - Pulegone

IPCS INCHEM -  Pulegone

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Pulegone

http://www.ebi.ac.uk/chebi/ -  Pulegone

http://www.ncbi.nlm.nih.gov/ -  Pulegone

http://dmd.aspetjournals.org/
(R)-(+)-Pulegone, the major monoterpene component of the abortifacient mint oil, pennyroyal oil, is metabolized by hepatic microsomal monooxygenases of the mouse to a hepatotoxin. The formation of a toxic metabolite is apparently mediated by cytochromes P-450 of the phenobarbital class inasmuch as phenobarbital pretreatment of mice increases, whereas beta-naphthoflavone pretreatment decreases, the extent of hepatic necrosis caused by pulegone. Furthermore, two inhibitors of cytochromes P-450, cobaltous chloride and piperonyl butoxide, block toxicity. An analog of (R)-(+)-pulegone that was labeled with deuterium in the allylic methyl groups was found to be significantly less hepatotoxic than the parent compound. The results indicate that oxidation of an allylic methyl group is required for generation of a hepatotoxic metabolite. Menthofuran was identified as a proximate toxic metabolite of (R)-(+)-pulegone, and investigations with (R)-(+)-pulegone-d6 and 18O2 strongly indicate that menthofuran is formed by a sequence of reactions that involve: 1) oxidation of an allylic methyl group, 2) intramolecular cyclization to form a hemiketal, and 3) dehydration to form the furan.

http://www.springerlink.com/
Citral extracted from Cymbopogon citratus (Gramineae) was subjected to photochemical epoxidation with hydrogen peroxide to obtain a mixture of epoxy derivatives at the C2=C3 and C6=C7 double bonds. The thermal oxidation of citral with m-chloroperoxybenzoic acid at room temperature gave only the corresponding 6,7-epoxy derivative as a mixture of E and Z isomers with respect to the C2=C3 double bond. Photosensitized oxygenation of citral in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll lead to a mixture of two isomeric hydroperoxides, (2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal and (2E,5E)-7-hydroperoxy-3,7-dimethylocta-2,5-dienal. Epoxidation of pulegone isolated from Penny royal oil (Mentha pulegium, Lamiaceae) with hydrogen peroxide under irradiation with a sodium lamp lead to a mixture of cis- and trans-isomeric 2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-ones, whereas under conditions of photosensitized oxygenation two hydroperoxide derivatives, 2-(1-hydroperoxy-1-methylethyl)-5-methylcyclohex-2-en-1-one and 2-hydroperoxy-5-methyl-2-(1-methylethenyl)cyclohexan-1-one, were also formed. Camphene reacted with hydrogen peroxide under irradiation to give a mixture of the corresponding endo- and exo-epoxy derivatives and camphor, while its thermal oxidation with m-chloroperoxybenzoic produced only the two former.

 

SALES SPECIFICATION

APPEARANCE

clear to yellowish liquid

PURITY

90.0% min

REFRACTIVE INDEX

1.485 - 1.490

SPECIFIC GRAVITY

0.932 - 0.938

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not regulated

HAZARD SYMBOL

  
PACKING GROUP  

 

SAFETY INFORMATION

HAZARD OVERVIEW

Combustible liquid and vapor. The toxicological properties of this material have not been fully investigated. May cause eye and skin irritation. May cause respiratory and digestive tract irritation.

GHS

  

SIGNAL WORD

Warning

PICTOGRAMS

HAZARD STATEMENTS

H302

PRECAUTIONARY STATEMENTS

 

EC DIRECTIVES

 
HAZARD CODES

Xn Harmful

RISK PHRASES

22

SAFETY PHRASES

 23-24/25

 

PACKING

 

 

PRICE INFORMATION