(+)-PULEGONE

Synonym(s):(+)-Pulegone;(R)-(+)-Pulegone;p-Menth-4(8)-en-3-one;(R)-p-Menth-4(8)-en-3-one;(R)-2-Isopropylidene-5-methylcyclohexanone

CAS NO.：89-82-7
Empirical Formula: C10H16O
Molecular Weight: 152.23
MDL number: MFCD00063000
EINECS: 201-943-2
SAFETY DATA SHEET (SDS)
Update Date: 2023-11-28 16:31:44

What is (+)-PULEGONE?

Chemical properties

clear colorless to yellow liquid

Chemical properties

Pulegone.has.a.pleasant.odor,somewhat.similar.to.peppermint.and.camphor.

Occurrence

The l-form is found in the essential oils of Agastache formosana, Israeli orange, Barosma betulina and Barosma crenulata; the d-form is the most abundant and is found in pennyroyal oils. Also reported found in rabbiteye blueberry, black currants (buds), fresh blackberry, heated blackberry, peppermint oil, corn mint oil, spearmint oil, Scotch spearmint oil, other Mentha oils, thyme, black tea, origanum, Ocimum basilicum varieties, rosemary, lemon balm, buchu oil, anise hyssop, sweet grass oil and German chamomile oil.

The Uses of (+)-PULEGONE

(R)-(+)-Pulegone may be used as a starting material to synthesize:

(2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro[5.5]undecane, a spiroketal
(R)-(+)-citronellic acid, an intermediate to prepare leucine-d₃
(+)-fawcettidine, a lycopodium alkaloid

The Uses of (+)-PULEGONE

A monoterpene, commonly found in the essential oils of Nepeta cataria (Catnip).

What are the applications of Application

(+)-Pulegone is a monoterpene compound found in a number of essential oils

Definition

ChEBI: The (5R)-enantiomer of p-menth-4(8)-en-3-one.

Aroma threshold values

Detection:.130.ppb..Aroma.characteristics.at.1.0%:.minty.cooling,.herbal.green,.sweet,.clean.spicy,.with. wintergreen.nuances.

Taste threshold values

Taste characteristics at 20 ppm: minty, terpy, cooling, woody pine, citrus lime, with fresh green peppermint notes.

General Description

(R)-(+)-Pulegone, a monoterpene ketone found in the essential oil of pennyroyal, can induce abortion.

Biochem/physiol Actions

Taste at 20 ppm

Synthesis

Isolated.from.pennyroyal.oil.(Moroccan.or.Spanish);.synthesis.from.3-methyl.cyclohexanone..The.structure.has.been.defined. by.the.work.of.several.authors;.the.d-,.l-.and.dl-forms.are.known;.the.dl-form.is.prepared.synthetically.and.is.not.found.in.nature.

Purification Methods

Purify pulegone via the semicarbazone which has m 174o (from MeOH) and [] D +68.2o (c 1, CHCl3). Fractionally distil it in vacuo. [Short & Read J Chem Soc 1309 1939]. [Erskine & Waight J Chem Soc 3425 1960, cf Ort Org Synth 65 203 1987, Beilstein 7 III 334, 7 IV 188.]

Properties of (+)-PULEGONE

Melting point:	<=25°C
Boiling point:	224 °C(lit.)
alpha	D20 +21°; 20546 +28.2°
Density	0.937 g/mL at 25 °C(lit.)
vapor pressure	138 mm Hg ( 25 °C)
refractive index	n20/D 1.488
FEMA	2963 \| PULEGONE
Flash point:	185 °F
storage temp.	2-8°C
solubility	Chloroform (Sparingly), Methanol (Slightly)
form	Liquid
color	Clear colorless to yellow
Specific Gravity	0.94
Odor	at 100.00 %. peppermint camphor fresh herbal buchu
optical activity	[α]20/D +23.5°, neat
λmax	255nm(lit.)
Merck	14,7937
JECFA Number	753
BRN	2040703
Dielectric constant	9.5（20℃）
CAS DataBase Reference	89-82-7(CAS DataBase Reference)
IARC	2B (Vol. 108) 2016
EPA Substance Registry System	d-Pulegone (89-82-7)

Safety information for (+)-PULEGONE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07 Health Hazard GHS08
GHS Hazard Statements	H302:Acute toxicity,oral H351:Carcinogenicity
Precautionary Statement Codes	P202:Do not handle until all safety precautions have been read and understood. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P308+P313:IF exposed or concerned: Get medical advice/attention.