13567-39-0

Basic information

• Product Name: 8,9-Epoxy cedrane
• Synonyms: cedr-8-ene epoxide;8,9-EPOXY CEDRANE;ANDRANE;ALPHA CEDRENE EPOXIDE;2abeta,3alpha,5aalpha,7beta,7aalpha)]-alph;7-Methanoazuleno[5,6-b]oxirene,octahydro-3,6,6,7a-tetramethyl-,[1aS-(1a.alpha.,2a.beta.,3.alpha.,2H-2a;7-methanoazuleno[5,6-b]oxirene,octahydro-3,6,6,7a-tetramethyl-2h-2[1as-(1a;[1aS-(1aalpha,2abeta,3alpha,5aalpha,7beta,7aalpha)]-octahydro-3,6,6,7a-tetramethyl-2H-2a,7-methanoazuleno[5,6-b]oxirene
• CAS NO: 13567-39-0
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.35
• EINECS: 236-971-4
• Product Categories: Industrial/Fine Chemicals
• Mol File: 13567-39-0.mol

Chemical Properties

• Boiling Point: 264.431 °C at 760 mmHg
• Flash Point: 96.568 °C
• Appearance: /
• Density: 1.045 g/cm³
• Vapor Pressure: 0.0159mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: 8,9-Epoxy cedrane(CAS DataBase Reference)
• NIST Chemistry Reference: 8,9-Epoxy cedrane(13567-39-0)
• EPA Substance Registry System: 8,9-Epoxy cedrane(13567-39-0)

Safety Data

• Hazardous Substances Data: 13567-39-0(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
8,9-Epoxy cedrane is used as a key ingredient in perfumes and colognes for its woody and floral scent, adding depth and complexity to fragrance compositions.
Used in Aromatherapy:
8,9-Epoxy cedrane is used as an aromatic compound in aromatherapy for its potential to evoke positive emotional responses and contribute to a relaxing atmosphere.
Used in Traditional Medicine:
8,9-Epoxy cedrane is used in traditional medicine due to its potential therapeutic properties, which are currently under investigation for various medicinal applications.
Used in Research and Development:
8,9-Epoxy cedrane is used as a subject of research for its unique chemical structure and aromatic properties, with the aim of discovering new applications in medicine and other fields.

InChI:InChI=1/C15H24O/c1-9-5-6-10-13(2,3)11-7-15(9,10)8-12-14(11,4)16-12/h9-12H,5-8H2,1-4H3

Upstream product

• 469-61-4 alpha-cedrene 

Relevant articles and documents

Novel and versatile photosensitized oxygenation reaction of α-cedrene

Three types of photosensitized oxygenations of α-cedrene (CED) were investigated, including: rose bengal(RB)-sensitized photooxygenation of α-cedrene in acetonitrile produced one major stereospecific product (cedr-8-exoen-9α-ol), in which the double bond migrated to an adjacent position, this result demonstrated the singlet oxygen process; 9,10-dicyanoanthrathene (DCA) sensitized photooxygenation led to the formation of cedr-8-en-10β-ol; benzyl (BZ)-sensitized photoepoxidation furnished a stereospecific 8α,9α-cedrene epoxide, this reaction includes radical reaction mechanism.

Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesvl diohosohate

We report the structures and stereochemistry of seven bisabolyl-derived sesquiterpenes arising from an unprecedented 1,6-cyclization (cisoid pathway) efficiently catalyzed by tobacco 5-epi-aristolochene synthase (TEAS). The use of (2Z,6E)-farnesyl diphosphate as an alternate substrate for recombinant TEAS resulted in a robust enzymatic cyclization to an array of products derived exclusively (≥99.5%) from the cisoid pathway, whereas these same products account for ca. 2.5% of the total hydrocarbons obtained using (2E,6E)-farnesyl diphosphate. Chromatographic fractionations of extracts from preparative incubations with the 2Z,6E substrate afforded, in addition to the acyclic allylic alcohols (2Z,6E)-farnesol (6.7%) and nerolidol (3.6%), five cyclic sesquiterpene hydrocarbons and two cyclic sesquiterpene alcohols: (+)-2-epiprezizaene (44%), (-)-α-cedrene (21.5%), (R)-(-)-β-curcumene (15.5%), R-acoradiene (3.9%), 4-epi-α-acoradiene (1.3%), and equal amounts of α-bisabolol (1.8%) and epi-R-bisalolol (1.8%). The structures, stereochemistry, and enantiopurities were established by comprehensive spectroscopic analyses, optical rotations, chemical correlations with known sesquiterpenes, comparisons with literature data, and GC analyses. The major product, (+)-2-epi-prezizaene, is structurally related to the naturally occurring tricyclic alcohol, jinkohol (2-epi-prezizaan-7 β-ol). Cisoid cyclization pathways are proposed by which all five sesquiterpene hydrocarbons are derived from a common (7R)-β-bisabolyl+/pyrophosphate - ion pair intermediate. The implications of the cisoid catalytic activity of TEAS are discussed.

Acid-catalyzed rearrangements of (-)-thujopsene

The transformations of (-)-thujopsene in liquid (HSO3F-SO2FCl) and over solid (TiO2/SO24) superacids, as well as by the action of peroxy acids, were studied. New tricyclic hydrocarbons were isolated.