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