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89-81-6

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89-81-6 Usage

Uses

Piperitone is a monoterpene compound that has a fresh minty camphor-like odour, and naturally occurs in extracts of commercial oil of peppermint. Piperitone is also used as a starting material in the synthesis of Thymol (T413000), a phenolic compound that is used for its antibacterial properties.

Definition

ChEBI: A p-menthane monoterpenoid that is cyclohex-2-en-1-one substituted by a methyl group at position 3 and an isopropyl group at position 6.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Check Digit Verification of cas no

The CAS Registry Mumber 89-81-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 9 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 89-81:
(4*8)+(3*9)+(2*8)+(1*1)=76
76 % 10 = 6
So 89-81-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3

89-81-6 Well-known Company Product Price

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  • TCI America

  • (P1783)  Piperitone (mixture of enantiomers, predominantly (R)-(-)-form)  >94.0%(GC)

  • 89-81-6

  • 25g

  • 320.00CNY

  • Detail
  • TCI America

  • (P1783)  Piperitone (mixture of enantiomers, predominantly (R)-(-)-form)  >94.0%(GC)

  • 89-81-6

  • 100g

  • 690.00CNY

  • Detail

89-81-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name piperitone

1.2 Other means of identification

Product number -
Other names PIPERTONE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:89-81-6 SDS

89-81-6Relevant articles and documents

Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation

Huang, David,Zhao, Yizhou,Newhouse, Timothy R.

supporting information, p. 684 - 687 (2018/02/09)

The use of allyl-palladium catalysis for the one-step α,β-dehydrogenation of ketones via their zinc enolates is reported. The optimized protocol utilizes commercially available Zn(TMP)2 as base and diethyl allyl phosphate as oxidant. Notably, this transformation operates under salt-free conditions and tolerates a diverse scope of cycloalkanones.

Hydrolytic enantioselective protonation of cyclic dienyl esters and a β-diketone with chiral phase-transfer catalysts

Yamamoto, Eiji,Gokuden, Daichi,Nagai, Ayano,Kamachi, Takashi,Yoshizawa, Kazunari,Hamasaki, Akiyuki,Ishida, Tamao,Tokunaga, Makoto

supporting information, p. 6178 - 6181 (2013/02/25)

Hydrolytic enantioselective protonation of dienyl esters and a β-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active α,β-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

Highly enantio- and s-trans C=C bond selective catalytic hydrogenation of cyclic enones: Alternative synthesis of (-)-menthol

Ohshima, Takashi,Tadaoka, Hiroshi,Hori, Kiyoto,Sayo, Noboru,Mashima, Kazushi

scheme or table, p. 2060 - 2066 (2009/04/07)

A highly enantioselective catalytic hydrogenation of cyclic enones was achieved by using the combination of a cationic Rh1 complex, (S)-5,5′-bis{di(3,5-di-tert-butyl-4-methoxyphenylphosphino)}-4, 4′-bi-1,3-benzodioxole (DTBM-SEGPHOS), and (CH2CH 2PPh3Br)2. The presence of an s-cis C=C bond isopropylidene moiety on the cyclic enone influenced the enantioselectivity of the hydrogenation. Thus, the hydrogenation of 3-alkyl-6-isopropylidene-2- cyclohexen-1-one, which contains both s-cis and s-trans enones, proceeded in excellent enantioselectivity (up to 98% ee). To obtain high enantio- and s-trans selectivities, the addition of a halogen source to the cationic Rh complex was the essential step. With the key step of the s-trans selective asymmetric hydrogenation of piperitenone, we demonstrated a new synthetic method for optically pure (-)-menthol via three atom-economical hydrogenations. Moreover, we found that the complete s-trans and s-cis C=C bond selective reactions were also realized by the proper choice of both the chiral ligands and halides.

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