5090-61-9

Basic information

• Product Name: (1R)-1,2,6,7,8,8a-Hexahydro-1,8aα-dimethyl-7β-(1-methylethenyl)naphthalene
• Synonyms: (1R)-1,2,6,7,8,8a-Hexahydro-1,8aα-dimethyl-7β-(1-methylethenyl)naphthalene;Nootkatene
• CAS NO: 5090-61-9
• Molecular Formula: C15H22
• Molecular Weight: 202.33518
• Mol File: 5090-61-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 288.5±30.0 °C(Predicted)
• Appearance: /
• Density: 0.91±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (1R)-1,2,6,7,8,8a-Hexahydro-1,8aα-dimethyl-7β-(1-methylethenyl)naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-1,2,6,7,8,8a-Hexahydro-1,8aα-dimethyl-7β-(1-methylethenyl)naphthalene(5090-61-9)
• EPA Substance Registry System: (1R)-1,2,6,7,8,8a-Hexahydro-1,8aα-dimethyl-7β-(1-methylethenyl)naphthalene(5090-61-9)

Safety Data

• Hazardous Substances Data: 5090-61-9(Hazardous Substances Data)

Usage

General Description

The chemical (1R)-1,2,6,7,8,8a-Hexahydro-1,8aα-dimethyl-7β-(1-methylethenyl)naphthalene, also known as α-Cedrene, is a naturally occurring sesquiterpene found in essential oils of cedarwood. It is a colorless to pale yellow liquid with a woody, balsamic, and cedar-like odor. α-Cedrene is used in the fragrance industry as an aromatic ingredient, particularly in perfumes, soaps, and cosmetics. It also has potential application in traditional medicine and aromatherapy due to its reported calming and stress-relieving properties. Additionally, α-Cedrene has shown promise in various industrial applications, including as a flavoring agent and in the production of insecticides and fungicides. Overall, α-Cedrene is a versatile compound with a wide range of potential uses.

Upstream product

• 10219-75-7 valencene 
• 4674-50-4 (+)-nootkatone 
• 840474-83-1 4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol 

Downstream Products

• 4674-50-4 (+)-nootkatone 

Relevant articles and documents

Iridium-catalysed highly selective reduction-elimination of steroidal 4-en-3-ones to 3,5-dienes in water

Steroidal 3,5-diene is an important structural motif in steroid drugs. In this report, an iridium-catalyzed reduction-elimination of readily available steroidal 4-en-3-ones is realized to prepare steroidal 3,5-dienes. At a low catalyst loading (S/C = 200), heating 4-en-3-ones in a water-mixed organic solvent with formic acid without inert atmosphere protection afforded the desired 3,5-dienes in moderate to excellent yields. In a gram-scale preparation, recrystallization is used instead of column chromatography to purify products. Excellent functionality tolerance and regioselectivity are featured. Structural moieties such as alkanols (primary, secondary and tertiary), esters (except for formate), tolylates, and ketones (endocyclic or exocyclic) are not affected. Surprisingly, the reduction-elimination only takes place at A-ring 4-en-3-ones. In addition, bicyclic 4-en-3-ones are also viable substrates. Synthetic applications of steroidal 3,5-dienes are demonstrated. Our method can also lead to steroidal 3,5-dienes-3-d (>99% d-incorporation) when DCO2D and D2O are used together.

The Rearrangement of Allylic Hydroperoxides Derived from (+)-Valencene

(+)-Valencene (I) reacts with triplet oxygen to give 84 percent of the secondary β-hydroperoxyde (II) and 15 percent of the α-hydroperoxide (III); reaction with singlet oxygen gives principally (ca. 80 percent) the tertiary β-hydroperoxide (IV).This undergoes a Schenck rearrangement to give suprafacially the β-hydroperoxide (II) by a non-dissociative mechanism which does not involve exchange of oxygen in an atmosphere of 18O2.The hydroperoxide (II) then undergoes a slower Smith epimerization to the α-hydroperoxide (III) by a dissociative mechanism which involves a substantial (> 55 percent) exchange.