(+)-Pulegone

ISO 17034:
Catalog Number : CS-T-40948
CAS Number : 89-82-7
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Product Information

Product Name : (+)-Pulegone
Category : API Standards
Molecular Weight : 152.23 mol/g
Molecular Formula : C10H16O
Application : "A monoterpene, commonly found in the essential oils of Nepeta cataria (Catnip)."

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Canonical SMILES : CC1CCC(=C(C)C)C(=O)C1
Isomeric SMILES : C[C@@H]1CCC(=C(C)C)C(=O)C1
InChI : InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1
InchIKey : NZGWDASTMWDZIW-MRVPVSSYSA-N
IUPAC Name : (5R)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
Exact Mass : 152.120115130
Color : Oil
Odor : Pleasant odor, midway between peppermint and camphor
Melting Point : <25°C
Boiling Point : 224.0 °C
Solubility : In water, 276 mg/L at 25 °C (est)
Density : 0.9323 at 20 °C
Chemical Classes : Biological Agents -> Plant Oils and Extracts
Use Classification : Flavoring Agents -> JECFA Flavorings Index
Hazard Class : Acute Tox. 4 (96.73%)
Description : (+)-pulegone is the (5R)-enantiomer of p-menth-4(8)-en-3-one.
EC Number : 201-943-2
Vapor Pressure : 0.12 mmHg
Antidoteand Emergency Treatment : The cases are presented of 3 adult women and a 22-month-old girl who experienced adverse effects following ingestion of pennyroyal (Mentha pulegium); the findings were placed in the context of previously reported cases of pennyroyal toxicity. One of the adult patients died after acute ingestion of pennyroyal. The infant was treated with gastric lavage within 30 min of ingestion, followed by 1 g/kg activated charcoal and 2 mL/kg sorbitol. She was then given 190 mg/kg oral acetylcysteine (N-acetylcysteine) followed by 70 mg/kg every 4 hr for a total of 17 doses. The other 2 patients ingested minimally toxic amounts of pennyroyal and recovered without receiving acetylcysteine. In the fatal case, a serum sample obtained 72 hr after acute ingestion contained 18 ng/mL pulegone and 1 ng/mL menthofuran. In a serum sample from the patient treated with acetylcysteine, obtained 10 hr after ingestion, the menthofuran level was 40 ng/mL.
Human Toxicity Excerpts : /SIGNS AND SYMPTOMS/ A review of cases of human intoxication with pennyroyal oil (Mentha pulegium: pulegone content 62-97%) indicate that ingestion of 10 mL resulted in moderate to severe toxicity and ingestion of greater than 15 mL (ca. 250 mg/kg bw for a 60 kg woman) resulted in death. The clinical pathology is characterised by massive centrilobular necrosis, pulmonary edema and internal hemorrhage.