18444-89-8

Basic information

• Product Name: methyl [3S-(3alpha,3aalpha,6alpha,8aalpha)]-octahydro-7,7-dimethyl-8-methylene-1H-3a,6-methanoazulene-3-carboxylate
• Synonyms: methyl [3S-(3alpha,3aalpha,6alpha,8aalpha)]-octahydro-7,7-dimethyl-8-methylene-1H-3a,6-methanoazulene-3-carboxylate;(3S)-2,3,4,5,6,7,8,8aα-Octahydro-7,7-dimethyl-8-methylene-1H-3aα,6α-methanoazulene-3α-carboxylic acid methyl ester;Methyl zizanoate
• CAS NO: 18444-89-8
• Molecular Formula: C₁₆H₂₄O₂
• Molecular Weight: 248.36056
• EINECS: 242-326-8
• Mol File: 18444-89-8.mol

Chemical Properties

• Boiling Point: 313.8°Cat760mmHg
• Flash Point: 136.4°C
• Appearance: /
• Density: 1.04g/cm³
• CAS DataBase Reference: methyl [3S-(3alpha,3aalpha,6alpha,8aalpha)]-octahydro-7,7-dimethyl-8-methylene-1H-3a,6-methanoazulene-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl [3S-(3alpha,3aalpha,6alpha,8aalpha)]-octahydro-7,7-dimethyl-8-methylene-1H-3a,6-methanoazulene-3-carboxylate(18444-89-8)
• EPA Substance Registry System: methyl [3S-(3alpha,3aalpha,6alpha,8aalpha)]-octahydro-7,7-dimethyl-8-methylene-1H-3a,6-methanoazulene-3-carboxylate(18444-89-8)

Safety Data

• Hazardous Substances Data: 18444-89-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl [3S-(3alpha,3aalpha,6alpha,8aalpha)]-octahydro-7,7-dimethyl-8-methylene-1H-3a,6-methanoazulene-3-carboxylate is used as an intermediate in the synthesis of pharmaceuticals for its unique molecular structure and properties.
Used in Fragrance Industry:
methyl [3S-(3alpha,3aalpha,6alpha,8aalpha)]-octahydro-7,7-dimethyl-8-methylene-1H-3a,6-methanoazulene-3-carboxylate is utilized as a building block in the creation of unique fragrances due to its azulene origin and complex molecular arrangement, which can contribute to novel scents and aromas.
Used in Flavor Industry:
Methyl [3S-(3alpha,3aalpha,6alpha,8aalpha)]-octahydro-7,7-dimethyl-8-methylene-1H-3a,6-methanoazulene-3-carboxylate is employed as a component in the development of distinctive flavors, taking advantage of its azulene-derived characteristics to enhance taste profiles.
Used in Chemical Research:
It serves as a subject of study in chemical research for its distinctive stereochemistry and potential to yield insights into the properties and behavior of complex organic molecules.

Upstream product

• 26934-85-0 (2R,4aS,5S,8R,8aS)-8a-Hydroxy-8-methanesulfonyloxy-1,1-dimethyl-octahydro-2,4a-methano-naphthalene-5-carboxylic acid methyl ester 
• 16202-83-8 4-Oxo-1-methoxycarbonyl-5,5-dimethyl-6α,7α-ethano-trans-hydrindan 
• 26560-72-5 (2R,4aS,5S,8R,8aS)-8,8a-Dihydroxy-1,1-dimethyl-octahydro-2,4a-methano-naphthalene-5-carboxylic acid methyl ester 
• 26560-34-9 (3S,3aR,6R,8aS)-7,7-Dimethyl-8-oxo-octahydro-3a,6-methano-azulene-3-carboxylic acid 
• 26560-71-4 (2R,4aS,5S)-1,1-Dimethyl-1,3,4,5,6,7-hexahydro-2H-2,4a-methano-naphthalene-5-carboxylic acid methyl ester 
• 43010-32-8 (3S,3aS,6R,8aS)-3-Hydroxymethyl-7,7-dimethyl-octahydro-3a,6-methano-azulen-8-ol 
• 16223-63-5 zizanoic alcohol 
• 186581-53-3 diazomethane 
• 16203-25-1 Zizanonsaeure 
• 33171-74-3 (3S,3aR,6R,8S,8aS)-8-Hydroxy-7,7,8-trimethyl-octahydro-3a,6-methano-azulene-3-carboxylic acid 
• 16203-25-1 (+)-zizanoic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 16223-63-5 zizanoic alcohol 
• 16203-25-1 (+)-zizanoic acid 
• 22387-78-6 methyl epizizanoate 
• 16223-63-5 epizizanoic alcohol 
• 82463-21-6 12-oxoepizizaene 
• 18444-94-5 (3S,3aS,6R,8aS)-3,7,7-trimethyl-8-methyleneoctahydro-1H-3a,6-methanoazulene 
• 38230-37-4 (+/-)-13-Thiophenylzizan-6-yl-benzoat 

Relevant articles and documents

Valorization of brazilian vetiver (Vetiveria zizanioides (L.) Nash ex Small) oil

The valorization of extracts from Brazilian vetiver (Vetiveria zizanioides (L.) Nash ex Small) roots was studied. This study took into account the extraction method, the chemical composition of the extracts, their sensorial characteristics, and the possibility of chemical transformations of the product. The performed extraction methods were hydrodistillation and extraction with supercritical carbon dioxide. Some pretreatment methods were tested on the vetiver roots and evaluated in terms of extraction yield, process time, chemical composition, and sensorial properties. Supercritical carbon dioxide extraction resulted in high yield (3.2%) in significantly less time than the other methods. The chemical compositions of the extracts obtained by the different methods were also compared to those of commercial vetiver oils from other sources, showing that Brazilian samples had a greater acid amount. An extraction in basic medium from Brazilian vetiver oil was done to remove its main acid (zizanoic acid), which was chemically transformed into an alcohol (khusimol) of desirable sensorial properties. Sensory evaluation indicated that the Brazilian volatile oil without acid could be used in perfumery and the extract obtained with supercritical carbon dioxide could have application in food.