491-09-8 Usage
Description
3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one, also known as p-Mentha-1,4(8)-dien-3-one, is a monoterpene found in various plants such as pennyroyal, spearmint, Scotch spearmint, citrus peel oils and juices, black currants, cardamom, origanum, buchu oil, lemon balm, and mastic gum fruit oil. It possesses a powerful, sharp, herbal minty, and phenolic odor with an aroma threshold value of 680 ppb. Piperitenone has been identified for its antioxidant activity, as it scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals in a cell-free assay (IC50 = 22.7 μg/ml) and inhibits peroxidation of linoleic acid.
Uses
Used in Flavor and Fragrance Industry:
3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one is used as a flavoring agent for its powerful, sharp, herbal minty, and phenolic odor. Its unique scent makes it suitable for creating various flavor profiles in the food and beverage industry.
Used in Aromatherapy:
Due to its strong aroma and herbal properties, 3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one can be used in aromatherapy as a component in essential oils or fragrances to provide a refreshing and invigorating experience.
Used in Cosmetics:
The unique scent and antioxidant properties of 3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one make it a potential ingredient in the cosmetics industry, where it can be used in the formulation of perfumes, colognes, and other fragranced products.
Used in the Pharmaceutical Industry:
Given its antioxidant activity and ability to scavenge DPPH radicals, 3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one may be utilized in the development of pharmaceutical products targeting oxidative stress-related conditions.
Used in the Agrochemical Industry:
The antioxidant properties of 3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one can also be harnessed in the agrochemical industry for the development of natural preservatives or additives to enhance the shelf life of agricultural products.
Synthesis Reference(s)
The Journal of Organic Chemistry, 52, p. 1505, 1987 DOI: 10.1021/jo00384a023
Check Digit Verification of cas no
The CAS Registry Mumber 491-09-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 1 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 491-09:
(5*4)+(4*9)+(3*1)+(2*0)+(1*9)=68
68 % 10 = 8
So 491-09-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3
491-09-8Relevant articles and documents
Chemoenzymatic Synthesis of the Intermediates in the Peppermint Monoterpenoid Biosynthetic Pathway
Cheallaigh, Aisling Ní,Mansell, David J.,Toogood, Helen S.,Tait, Shirley,Lygidakis, Antonios,Scrutton, Nigel S.,Gardiner, John M.
, p. 1546 - 1552 (2018/08/04)
A chemoenzymatic approach providing access to all four intermediates in the peppermint biosynthetic pathway between limonene and menthone/isomenthone, including noncommercially available intermediates (-)-trans-isopiperitenol (2), (-)-isopiperitenone (3), and (+)-cis-isopulegone (4), is described. Oxidation of (+)-isopulegol (13) followed by enolate selenation and oxidative elimination steps provides (-)-isopiperitenone (3). A chemical reduction and separation route from (3) provides both native (-)-trans-isopiperitenol (2) and isomer (-)-cis-isopiperitenol (18), while enzymatic conjugate reduction of (-)-isopiperitenone (3) with IPR [(-)-isopiperitenone reductase)] provides (+)-cis-isopulegone (4). This undergoes facile base-mediated chemical epimerization to (+)-pulegone (5), which is subsequently shown to be a substrate for NtDBR (Nicotiana tabacum double-bond reductase) to afford (-)-menthone (7) and (+)-isomenthone (8).
Method for producing 1-menthol
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Example 3, (2008/06/13)
Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.
Method for producing 1-menthol
-
, (2008/06/13)
Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.
