18374-76-0

Basic information

• Product Name: 3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one
• Synonyms: (-)-Rotundone;(3S)-3,4,5,6,7,8-Hexahydro-3,8α-dimethyl-5α-(1-methylethenyl)azulen-1(2H)-one;3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one
• CAS NO: 18374-76-0
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.33458
• Mol File: 18374-76-0.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 128-129 °C
• Appearance: /
• Density: 0.96±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one(18374-76-0)
• EPA Substance Registry System: 3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one(18374-76-0)

Safety Data

• Hazardous Substances Data: 18374-76-0(Hazardous Substances Data)

Usage

Description

3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one is a complex organic compound with a unique molecular structure. It is characterized by its hexahydroazulene core, which is a type of bicyclic compound with six hydrogen atoms attached to its ring structure. 3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one also features two methyl groups at the 3α and 8α positions, as well as a 1-methylethenyl group at the 5α position. This complex structure likely contributes to its potential applications in various industries.

Uses

Used in Flavor and Fragrance Industry:
3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one is used as a flavoring agent for its spicy, peppery aroma. It is extracted from Cyperus rotundus and is particularly valued for its unique scent profile, which can be used to enhance the flavor of various food products and beverages.
Used in Perfumery:
In the perfumery industry, 3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one is used as a fixative agent to help stabilize and prolong the scent of perfumes and fragrances. Its spicy, peppery aroma can also be used to add depth and complexity to fragrance compositions.
Used in Aromatherapy:
3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one may also find use in aromatherapy, where its spicy, peppery aroma can be used to create a stimulating and invigorating atmosphere. 3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one's unique scent profile may have potential therapeutic benefits, such as promoting relaxation or enhancing mood.
Used in Cosmetics and Personal Care Products:
Due to its unique aroma, 3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one can be used in cosmetics and personal care products, such as soaps, lotions, and creams, to provide a distinctive and appealing scent. Its potential use in these products may also be due to its ability to act as a fixative, helping to maintain the fragrance of these products over time.
Used in the Wine Industry:
3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one is found in Australian wine made from syrah (shiraz) grape. Its presence contributes to the unique and complex aroma profile of this type of wine, enhancing the overall sensory experience for consumers. 3,4,5,6,7,8-Hexahydro-3α,8α-dimethyl-5α-(1-methylethenyl)azulene-1(2H)-one may be used to add depth and complexity to the flavor of wines, making it a valuable component in the winemaking process.

Upstream product

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Relevant articles and documents

GUAIANE SESQUITERPENES FROM AGARWOOD

Key Word Index - Aquilaria agallocha; Thymelaeaceae; agarwood; sesquiterpenes; (-)-guaia-1(10),11-dien-15-ol; (-)-guaia-1(10),11-diene-15-carboxylic acid; methyl guaia-1(10),11-diene-15-carboxylate; (+)-guaia-1(10),11-dien-9-one; (-)-1,10-epoxyguai-11-ene; (-)-guaia-1(10),11-dien-15,2-olide; (-)-rotundone.Seven new sesquiterpenes, all of which have a guaiane skeleton, i.e. (-)-guaia-1(10),11-dien-15-ol, (-)-guaia-1(10),11-diene-15-carboxylic acid, methyl guaia-1(10),11-diene-15-carboxylate, (+)-guaia-1(10),11-dien-9-one, (-)-1,10-epoxyguai-11-ene, (-)-guaia-1(10),11-dien-15,2-olide and (-)-rotundone, have been isolated from Aquilaria agallocha (agarwood).Their structures have been established on the bases of detailed spectroscopic analyses and synthesis.

Development of a synthesis method for odor sesquiterpenoid, (?)-rotundone, using non-heme Fe2+-chelate catalyst and ferric-chelate reductase

(?)-Rotundone, a sesquiterpenoid that has a characteristic woody and peppery odor, is a key aroma component of spicy foodstuffs, such as black pepper and Australian Shiraz wine. (?)-Rotundone shows the lowest level of odor threshold in natural compounds and remarkably improves the quality of various fruit flavors. To develop a method for the synthesis of (?)-rotundone, we focused on non-heme Fe2+-chelates, which are biomimetic catalysts of the active center of oxygenases and enzymatic supply and regeneration of those catalysts. That is, we constructed a unique combination system composed of the oxidative synthesis of (?)-rotundone using the non-heme Fe2+-chelate catalyst, Fe(II)-EDTA, and the enzymatic supply and regeneration of Fe2+-chelate by ferric-chelate reductase, YqjH, from Escherichia coli. In addition, we improved the yield of (?)- rotundone by the application of cyclodextrin and glucose dehydrogenase to this system, and thus established a platform for efficient (?)-rotundone production.

PRODUCTION OF GUAIENE AND ROTUNDONE

Proposed is a process for producing rotundone from α-guaiene, in particular by oxidation of the C(3) position, wherein the α-guaiene is produced from a precursor by a sesquiterpene synthase. The sesquiterpene synthase is produced in a microorganism.

Identification of Rotundone as a Potent Odor-Active Compound of Several Kinds of Fruits

An investigation of the aromas of grapefruit, orange, apple, and mango revealed the presence of an odor-active compound that gave off a strong woody odor when assessed by gas chromatography-olfactometry. We isolated the compound from a high-boiling fraction of an orange essential oil, and subsequent nuclear magnetic resonance analyses of the isolated compound identified it as rotundone. Mass spectra and retention indices obtained from aroma concentrates of grapefruit, apple, and mango were identical to those of rotundone, which was therefore determined to be the common woody compound in these fruits. Sensory analyses were performed to assess the effects of rotundone on model beverages of the various fruits. It was revealed that rotundone added at even subthreshold levels to model beverages did not confer directly the woody odor, but had significant effects on the overall flavors of the beverages, helping them to better approximate the natural flavors of the fruits.