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W296309

Sigma-Aldrich

(R)-(+)-Pulegone

≥90%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
89-82-7
Molecular Weight:
152.23
FEMA Number:
2963
Beilstein:
2040703
EC Number:
201-943-2
Council of Europe no.:
2050c
MDL number:
MFCD00063000
UNSPSC Code:
12164502
PubChem Substance ID:
24901423
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

Kosher

vapor pressure

138 mmHg ( 25 °C)

Assay

≥90%

optical activity

[α]20/D +22°, neat

refractive index

n20/D 1.486 (lit.)

bp

224 °C (lit.)

density

0.937 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

herbaceous; minty; sulfurous; sweet

SMILES string

C[C@@H]1CC\C(=C(\C)C)C(=O)C1

InChI

1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1

InChI key

NZGWDASTMWDZIW-MRVPVSSYSA-N

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Biochem/physiol Actions

Taste at 20 ppm

Other Notes

Natural occurrence: Buchu oil, native spearmint, pennyroyal, peppermint, scotch spearmint and thyme.

Disclaimer

For R&D or non-EU Food use. Not for retail sale.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

179.6 °F - closed cup

Flash Point(C)

82 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP6321
SHBN2323
SHBL3490
SHBM0808
SHBL0645

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Mosciano, G.
Perfumer & Flavorist, 30, 56-56 (2005)
Feng Li et al.
Chemical research in toxicology, 24(5), 744-751 (2011-04-08)
A predominant pathway of xenobiotic-induced toxicity is initiated by bioactivation. Characterizing reactive intermediates will provide information on the structure of reactive species, thereby defining a potential bioactivation mechanism. Because most reactive metabolites are not stable, it is difficult to detect
Charalabos D Kanakis et al.
Phytochemical analysis : PCA, 23(1), 34-43 (2011-05-28)
Mentha pulegium L. (pennyroyal) is one of the four most commercially important Mentha species, even it is not a cultivated plant. It can be abundantly located in the Iberian Peninsula and North African countries. In Greece it grows in the
Pedro Marcos Gomes Soares et al.
The Journal of pharmacy and pharmacology, 64(12), 1777-1784 (2012-11-14)
We evaluated the relaxant activity of the essential oil of Mentha pulegium L. (EOMP) and pulegone in rat isolated tracheal and bladder smooth muscles. ISOMETRIC contractions of isolated tracheal and bladder strips from male Wistar rats were induced by KCl
Maung Kyaw Moe Tun et al.
The Journal of organic chemistry, 77(20), 9422-9425 (2012-10-04)
A three-step synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one (1) from (R)-(+)-pulegone (3), proceeding in 44% overall yield, is described. The sequence comprises vinyl triflate formation, site-selective ozonolysis, and reduction. The route requires only one chromatographic purification and provides a convenient method to access
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