(+)-PULEGONE

(+)-PULEGONE Basic information
Product Name:(+)-PULEGONE
Synonyms:(R)-(+)-P-MENTH-4(8)-EN-3-ONE;(R)-P-MENTH-4(8)-EN-3-ONE;(R)-(+)-PULEGONE;(R)-PULEGONE;(R)-(+)-5-METHYL-2-ISOPROPYLIDENCYCLOHEXANONE;(R)-2-ISOPROPYLIDENE-5-METHYLCYCLOHEXANONE;R-(+)-2-ISOPROPYLIDENE-5-METHYLCYCLOHEXANONE;PULEGON
CAS:89-82-7
MF:C10H16O
MW:152.23
EINECS:201-943-2
Product Categories:Biochemistry;Monocyclic Monoterpenes;Aromatic Ketones (substituted);Terpenes;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:89-82-7.mol
(+)-PULEGONE Structure
(+)-PULEGONE Chemical Properties
Melting point <=25°C
alpha D20 +21°; 20546 +28.2°
Boiling point 224 °C(lit.)
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
Fp 185 °F
storage temp. 2-8°C
solubility Chloroform (Sparingly), Methanol (Slightly)
form Liquid
color Clear colorless to yellow
Specific Gravity0.94
Odorat 100.00 %. peppermint camphor fresh herbal buchu
Odor Typeminty
optical activity[α]20/D +23.5°, neat
λmax255nm(lit.)
Merck 14,7937
JECFA Number753
BRN 2040703
InChIKeyNZGWDASTMWDZIW-MRVPVSSYSA-N
LogP2.56
CAS DataBase Reference89-82-7(CAS DataBase Reference)
IARC2B (Vol. 108) 2016
EPA Substance Registry Systemd-Pulegone (89-82-7)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 23-24/25
RIDADR 2810
WGK Germany 3
RTECS OT0261000
10-23
HS Code 2914 29 00
HazardClass 6.1(b)
PackingGroup III
Hazardous Substances Data89-82-7(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 470 mg/kg LD50 dermal Rabbit 3090 mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
(+)-PULEGONE Usage And Synthesis
Chemical Propertiesclear colorless to yellow liquid
Chemical PropertiesPulegone.has.a.pleasant.odor,somewhat.similar.to.peppermint.and.camphor.
OccurrenceThe 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.
UsesA monoterpene, commonly found in the essential oils of Nepeta cataria (Catnip).
DefinitionChEBI: The (5R)-enantiomer of p-menth-4(8)-en-3-one.
Aroma threshold valuesDetection:.130.ppb..Aroma.characteristics.at.1.0%:.minty.cooling,.herbal.green,.sweet,.clean.spicy,.with. wintergreen.nuances.
Taste threshold valuesTaste 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 ActionsTaste at 20 ppm
SynthesisIsolated.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.
targetGABA Receptor
Purification MethodsPurify 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.]
(+)-PULEGONE Preparation Products And Raw materials
Preparation ProductsMenthone-->p-Mentha-8-thiol-3-one-->Huperzine B-->Cyclopentanecarboxylic acid, 2-methyl-5-(1-methylethylidene)-, ethyl ester, (2R)- (9CI)
Cantharidin benzoylpaeoniflorin RehMapicroside 1,8-Cineole (+)-MENTHOL benzoyloxypaeoniflorin alpha-Terpineol DL-Menthol Borneol Albiflorin Pulegone semicarbazone Pennyroyal,NLT84%Pulegone,Pennyroyal84%min.Pulegone Menthone (+)-PULEGONE = R-P-MENTH-4(8)-EN-3-ONE p-Mentha-8-thiol-3-one trans-Pulegone oxide,cis-Pulegone oxide S-(-)-PULEGONE Z(+)-Pulegone

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