22771-44-4

Basic information

• Product Name: 1-methyl-4-prop-1-en-2-yl-cyclohex-2-en-1-ol
• Synonyms: 1-methyl-4-prop-1-en-2-yl-cyclohex-2-en-1-ol;PARA-MENTHA-2,8-DIEN-1-OL;p-Mentha-2,8-dien-1-ol;trans-p-Menthane-2,8-diene-1-ol;D-2,8-P-MENTHADIEN-1-OL
• CAS NO: 22771-44-4
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• Mol File: 22771-44-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 216.9°Cat760mmHg
• Flash Point: 87°C
• Appearance: /
• Density: 0.947g/cm³
• Vapor Pressure: 0.0294mmHg at 25°C
• Refractive Index: 1.494
• PKA: 14.66±0.40(Predicted)
• CAS DataBase Reference: 1-methyl-4-prop-1-en-2-yl-cyclohex-2-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-4-prop-1-en-2-yl-cyclohex-2-en-1-ol(22771-44-4)
• EPA Substance Registry System: 1-methyl-4-prop-1-en-2-yl-cyclohex-2-en-1-ol(22771-44-4)

Safety Data

• Hazardous Substances Data: 22771-44-4(Hazardous Substances Data)

Usage

Description

1-methyl-4-prop-1-en-2-yl-cyclohex-2-en-1-ol, also known as carvone, is a naturally occurring chiral monoterpene with a distinctive minty or caraway aroma. It is a colorless to very slightly yellow oily liquid and is found in caraway seed oil and gingergrass. Carvone exhibits a medium strength odor and is characterized by its terpinoid fragrance.

Uses

Used in Flavor Industry:
1-methyl-4-prop-1-en-2-yl-cyclohex-2-en-1-ol is used as a flavoring agent for its characteristic minty or caraway aroma. It is commonly utilized in the food and beverage industry to add a refreshing and distinctive taste to various products.
Used in Fragrance Industry:
1-methyl-4-prop-1-en-2-yl-cyclohex-2-en-1-ol is used as a fragrance ingredient due to its medium strength odor and minty terpenic type. It is often employed in the creation of perfumes, colognes, and other scented products to provide a fresh and invigorating scent.
Used in Essential Oils:
1-methyl-4-prop-1-en-2-yl-cyclohex-2-en-1-ol is used in the production of essential oils, particularly caraway seed oil and gingergrass oil, where it contributes to the overall aroma and therapeutic properties of the oils.
Used in Aromatherapy:
1-methyl-4-prop-1-en-2-yl-cyclohex-2-en-1-ol is used in aromatherapy for its potential calming and invigorating effects. The minty aroma of carvone can help to promote relaxation and mental clarity, making it a popular choice for use in aromatherapy practices.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, carvone has been studied for its potential medicinal properties, such as its ability to act as an insect repellent and its use in the treatment of digestive issues. It may be used in the development of pharmaceutical products for these purposes.

InChI:InChI=1/C10H16O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,9,11H,1,5,7H2,2-3H3

Upstream product

• 138-86-3 limonene. 
• 1686-14-2 α-pinene epoxide 
• 5989-27-5 D-limonene 
• 74756-09-5 1α-hydroxy-2β-phenylseleno-trans-p-menth-8-ene 
• 106-25-2 Nerol 
• 106-24-1 Geraniol 
• 1195-92-2 Limonene oxide 

Downstream Products

• 68754-14-3 1-acetoxy-trans-p-mentha-2,8-diene 
• 16750-82-6 (S)-isopiperitenone 
• 6252-34-2 6-(1'-hydroxyisopropyl)-3-methyl-2-cyclohexenol 
• 83217-89-4 4(15)-eudesmene-1β,11-diol 
• 71697-77-3 6β-(2'-hydroxyisopropyl)-3-methyl-2-cyclohexenone 
• 14132-18-4 6,6,9-Trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 16849-50-6 tetrahydrocannabinol 
• 536697-79-7 abn-cannabidiol 
• 3556-78-3 cannabidiol 
• 43009-38-7 (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 6909-05-3 iso-Δ⁸-tetrahydrocannabinol 

Relevant articles and documents

A Novel Cyclization of Geraniol and Nerol Initiated by Tris(p-bromophenyl)ammoniumyl Radical Cation

Geraniol (1) and nerol (2) undergo a novel cyclization to cis-p-mentha-2,8-dien-1-ol (4) by reaction with tris(pbromophenyl)ammoniumyl radical cation (3) and the reaction mechanism is discussed.

Continuous flow photooxygenation of monoterpenes

Photooxygenation of monoterpenes was conducted in two continuous flow reactors. The first, suitable for lab-scale research, had a maximum yield of 99.9%, and the second, focused on industrial applications, showed a daily output that was 270.0-fold higher than that in batch systems. The use of sunlight instead of an LED lamp gave 68.28% conversion.

Selective photosensitized oxidation and its catalytic regulation of monoterpene with molecular oxygen in different reaction media

The photo-catalytic oxidation of α-pinene, β-pinene and limonene with molecular oxygen sensitized by tetrachlorotetraiodo-fluorescein sodium salt (RB) has been studied in different reaction media under green light irradiation. Simple and efficient photosensitized oxidation equipment was employed successfully to improve the efficiency of the photosensitized reaction. The results indicate that the photosensitized oxidation products can be directly obtained without after-treatment by reductive reagent. Furthermore, it was found that the product distributions are remarkably affected by reaction media, and that N,N-dimethylformamide (DMF) can regulate the selectivity to products. In particular, the good selectivity (85%) to the main product (myrtenal) and the excellent conversion (99%) were obtained in the absence of any other catalysts when DMF was used as reaction solvent in the photosensitized oxidation of β-pinene. Moreover, the possible photosensitized oxidation reaction mechanism in different media was suggested in the present work.