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| (+)-PULEGONE Basic information |
| (+)-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 Gravity | 0.94 | | optical activity | [α]20/D +23.5°, neat | | λmax | 255nm(lit.) | | Merck | 14,7937 | | JECFA Number | 753 | | BRN | 2040703 | | InChIKey | NZGWDASTMWDZIW-MRVPVSSYSA-N | | CAS DataBase Reference | 89-82-7(CAS DataBase Reference) | | IARC | 2B (Vol. 108) 2016 | | EPA Substance Registry System | d-Pulegone (89-82-7) |
| Hazard Codes | Xn | | Risk Statements | 22 | | Safety Statements | 23-24/25 | | RIDADR | 2810 | | WGK Germany | 3 | | RTECS | OT0261000 | | F | 10-23 | | HS Code | 2914 29 00 | | HazardClass | 6.1(b) | | PackingGroup | III | | Hazardous Substances Data | 89-82-7(Hazardous Substances Data) | | Toxicity | LD50 orally in Rabbit: 470 mg/kg LD50 dermal Rabbit 3090 mg/kg |
| (+)-PULEGONE Usage And Synthesis |
| 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.] |
| (+)-PULEGONE Preparation Products And Raw materials |
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