Pulegone

Pulegone: Pulegone^[1]

IUPAC name

(R)-5-Methyl-2-(1-methylethylidine)cyclohexanone

Other names

p-Menth-4(8)-en-3-one;
δ-4(8)-p-menthen-3-one;
(R)-2-Isopropylidene-5-methylcyclohexanone;
(R)-p-Menth-4(8)-en-3-one;
(R)-(+)-Pulegone

Identifiers

CAS number 89-82-7^Y

PubChem 442495

ChemSpider 390923^Y

UNII 4LF2673R3G^Y

ChEBI CHEBI:35596^Y

Jmol-3D images Image 1

SMILES

O=C1/C(=C(/C)C)CC[C@@H](C)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^Y
Key: NZGWDASTMWDZIW-MRVPVSSYSA-N^Y

Properties

Molecular formula C₁₀H₁₆O

Molar mass 152.23 g/mol

Appearance Colorless oil

Density 0.9346 g/cm³

Boiling point
224 °C, 497 K, 435 °F

Solubility in water Insoluble

Solubility in Ethanol
Ether
Chloroform Miscible

Hazards

MSDS MSDS^[2]

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita, and pennyroyal.^[3]^[4] It is classified as a monoterpene.

Pulegone is a clear colorless oily liquid and has a pleasant odor similar to pennyroyal, peppermint and camphor. It is used in flavoring agents, in perfumery, and in aromatherapy.

Contents

1 Toxicology

2 Plants that contain the chemical

3 Notes and references

4 See also

Toxicology

It was reported that the chemical is toxic to rats if a large quantity is consumed.^[5] Asekun et al. found that the chemical content of Mentha longifolia L was decreased by the treatments at high temperatures, suggesting that the herb should be oven dried or thoroughly cooked before consumption.^[6]

Plants that contain the chemical

Mentha longifolia ^[6]

Pennyroyal ^[7]

Peppermint ^[8]

Notes and references

^ Merck Index, 11th Edition, 7955.

^ Universiti Malaysia Pahang. "Safety data sheet". http://notes.ump.edu.my/fkksa/FKKSA/Archive/Technical%20Unit/Warehouse%20Unit/Chemical/MSDS/MERCK_EN/8186/818665.pdf. Retrieved 8 June 2009.

^ Grundschober, F. (1979) Literature review of pulegone. Perfum. Flavorist, 4, 15–17.

^ Sullivan, J.B., Rumack, B.H., Thomas, H., Peterson, R.G. & Brysch, P. (1979) Pennyroyal oil poisoning and hepatotoxicity. J. Am. Med. Assoc., 242, 2873–2874.

^ Thorup, I. et al.; Würtzen, G; Carstensen, J; Olsen, P (1983). "Short term toxicity study in rats dosed with pulegone and menthol". Toxicology Letters 19 (3): 207–210. doi:10.1016/0378-4274(83)90120-0. PMID 6658833.

^ ^a ^b Asekun, O.T. et al.; Grierson, D; Afolayan, A (2006). "Effects of drying methods on the quality and quantity of the essential oil of Mentha longifolia L. subsp. Capensis". Food Chemistry 101 (3): 995–998. doi:10.1016/j.foodchem.2006.02.052.

^ Gordon, W. Perry et al.; Valerie Howland (1982). "Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse". Toxicology and Applied Pharmacology 65 (3): 413–424. doi:10.1016/0041-008X(82)90387-8. PMID 7157374.

^ Farley, Derek R.; Valerie Howland (2006). "The natural variation of the pulegone content in various oils of peppermint". Journal of the Science of Food and Agriculture 31 (11): 1143–1151. doi:10.1002/jsfa.2740311104.

See also

Cerebellum

Creatinine

Doebner-Miller reaction

Isopulegone

Menthofuran

(+)-Menthofuran

Menthol

Pennyroyal

(−)-Pulegone

Categories:
Ketones
Flavors
Perfume ingredients
Monoterpenes

Pulegone^[1]

IUPAC name (R)-5-Methyl-2-(1-methylethylidine)cyclohexanone
Other names p-Menth-4(8)-en-3-one; δ-4(8)-p-menthen-3-one; (R)-2-Isopropylidene-5-methylcyclohexanone; (R)-p-Menth-4(8)-en-3-one; (R)-(+)-Pulegone
Identifiers
CAS number	89-82-7^Y
PubChem	442495
ChemSpider	390923^Y
UNII	4LF2673R3G^Y
ChEBI	CHEBI:35596^Y
Jmol-3D images	Image 1
SMILES O=C1/C(=C(/C)C)CC[C@@H](C)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^Y Key: NZGWDASTMWDZIW-MRVPVSSYSA-N^Y
Properties
Molecular formula	C₁₀H₁₆O
Molar mass	152.23 g/mol
Appearance	Colorless oil
Density	0.9346 g/cm³
Boiling point	224 °C, 497 K, 435 °F
Solubility in water	Insoluble
Solubility in Ethanol Ether Chloroform	Miscible
Hazards
MSDS	MSDS^[2]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

pulégone — ● pulégone nom féminin Cétone monoterpénique C10H16O, contenue dans l essence de menthe pouliot et employée en parfumerie. (Son hydrogénation donne la menthone.) … Encyclopédie Universelle
pulegone — pulegonas statusas T sritis chemija formulė (CH₃)₂C=C₆H₇(=O)CH₃ atitikmenys: angl. pulegone rus. пулегон ryšiai: sinonimas – 2 izopropiliden 5 metilcikloheksanonas … Chemijos terminų aiškinamasis žodynas
pulegone — noun A monoterpenoid ketone, found in pennyroyal, that is toxic to dogs and cats … Wiktionary
pulegone — pu·le·gone … English syllables
pulegone — ˌgōn noun ( s) Etymology: International Scientific Vocabulary puleg (from New Latin pulegium, specific epithet of Mentha pulegium, from Latin puleium, pulegium pennyroyal) + one : a fragrant liquid terpenoid ketone C10H16O derived from menthenone … Useful english dictionary
Peppermint — This article is about the herb. For the tree commonly known as peppermint, see Agonis flexuosa. For the Linux operating system, see Peppermint OS. Peppermint Peppermint (Mentha x piperita) … Wikipedia
Doebner-Miller reaction — The Doebner Miller reaction is the organic reaction of an aniline with α,β unsaturated carbonyl compounds to form quinolines. [Doebner, O.; Miller, W. v. Ber. 1881, 14 , 2812.] [Doebner, O.; Miller, W. v. Ber. 1883, 16 , 1664 2464.] [Doebner, O.; … Wikipedia
Doebner–Miller reaction — The Doebner Miller reaction is the organic reaction of an aniline with α,β unsaturated carbonyl compounds to form quinolines.[1][2][3][4] … Wikipedia
Menthol — Not to be confused with methanol. Menthol … Wikipedia
oil — An inflammable liquid, of fatty consistency and unctuous feel, which is insoluble in water, soluble or insoluble in alcohol, and freely soluble in ether. Oils are variously classified as animal … Medical dictionary

Academic Dictionaries and Encyclopedias

Pulegone

Contents

Toxicology

Plants that contain the chemical

Notes and references

See also

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Academic Dictionaries and Encyclopedias

Wikipedia

Pulegone

Contents

Toxicology

Plants that contain the chemical

Notes and references

See also

Look at other dictionaries:

Share the article and excerpts

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