18409-17-1

Basic information

• Product Name: trans-2-Octen-1-ol
• Synonyms: (2E)-2-Octen-1-ol;(E)-2-octenol;2-Octen-1-ol, (E)-;trans-1-oct-2-enol;trans-2-Octenol;FEMA 3887;(2E)-OCTEN-1-OL;2-OCTEN-1-OL
• CAS NO: 18409-17-1
• Molecular Formula: C₈H₁₆O
• Molecular Weight: 128.21
• EINECS: 242-288-2
• Product Categories: Acyclic;Alkenes;Organic Building Blocks;Alphabetical Listings;Flavors and Fragrances;O-P
• Mol File: 18409-17-1.mol
• Article Data: 55

Chemical Properties

• Melting Point: -31.5°C (estimate)
• Boiling Point: 85-87 °C10 mm Hg(lit.)
• Flash Point: 198 °F
• Appearance: colorless/Liquid
• Density: 0.843 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.107mmHg at 25°C
• Refractive Index: n20/D 1.4460(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.49±0.10(Predicted)
• Water Solubility: Insoluble
• BRN: 1720707
• CAS DataBase Reference: trans-2-Octen-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: trans-2-Octen-1-ol(18409-17-1)
• EPA Substance Registry System: trans-2-Octen-1-ol(18409-17-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-36/37-37/39
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• Hazardous Substances Data: 18409-17-1(Hazardous Substances Data)

Usage

Description

Trans-2-Octen-1-ol is a clear colorless liquid with a distinct aroma. It is characterized by a green, slightly oxidized, oily, and nutty scent, with additional notes of chicken fatty, goaty, and creamy nuances. trans-2-Octen-1-ol is also reminiscent of cucumber rind and has a taste threshold value ranging from 1 to 5 ppm.

Uses

Used in Flavor and Fragrance Industry:
Trans-2-Octen-1-ol is used as a flavoring agent for its unique taste and aroma characteristics. It is particularly valued for its ability to impart a green, slightly oxidized, oily, and nutty flavor to various products.
Used in the Food Industry:
Trans-2-Octen-1-ol is used as an additive in the food industry to enhance the taste and aroma of products. It is commonly found in apple, bilberry, cranberry, guava, orange, grape, melon, peas, strawberry jam, potato, roasted turkey, and chicken, providing a distinct flavor profile to these items.
Used in the Beverage Industry:
In the beverage industry, trans-2-Octen-1-ol is used to add a unique flavor and aroma to drinks such as cognac and rum. Its presence contributes to the overall taste and sensory experience of these beverages.
Used in the Perfumery Industry:
Trans-2-Octen-1-ol is also utilized in the creation of perfumes and fragrances due to its distinct and complex scent. It can be used to add depth and nuance to various fragrance compositions.
Used in the Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, trans-2-Octen-1-ol's unique properties may also make it a candidate for use in the pharmaceutical industry, potentially for the development of new drugs or as a component in drug delivery systems.

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 2715, 1973 DOI: 10.1021/ja00789a068Tetrahedron Letters, 19, p. 1145, 1978

InChI:InChI=1/C8H16O/c1-2-3-4-5-6-7-8-9/h6-7,9H,2-5,8H2,1H3

Upstream product

• 2548-87-0 (E)-2-Octenal 
• 2351-90-8 ethyl (2E)-oct-2-enoate 
• 1871-67-6 (E)-oct-2-enoic acid 
• 693-03-8 n-butyl magnesium bromide 
• 18913-31-0 2,3-butadien-1-ol 
• 20739-58-6 2-octyn-1-ol 
• 41285-63-6 bis-(1,2-dimethyl-propyl)-oct-1-enyl-borane 
• 16722-09-1 trimethylsilyloxirane 
• 16823-63-5 phenyl hexyl sulfone 
• 7045-86-5 2-methyl-4,7-dihydro-1,3-dioxepine 
• 1003-83-4 2,2-dimethyl-4,7-dihydro-1,3-dioxepin 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 106-70-7 methyl hexanoate 
• 100808-08-0 (E)-oct-2-enoic acid chloride 

Downstream Products

• 2548-87-0 (E)-2-Octenal 
• 56318-83-3 (E)-1-bromo-oct-2-ene 
• 106708-08-1 (E)-2-octenyl p-toluenesulfinate 
• 2548-87-0 2-octen-1-al 
• 132747-06-9 (2R,3S)-3-pentyloxiranecarboxylic acid 
• 142-62-1 hexanoic acid 
• 2371-13-3 1-acetoxyoct-2-ene 
• 3913-80-2 (E)-2-octen-1-yl acetate 
• 113120-17-5 Toluene-4-sulfonic acid (E)-oct-2-enyl ester 
• 84700-65-2 methyl rac-9-oxo-15-(phenylsulfinyl)-14(E)-prostanoate 
• 28593-20-6 1-(4-fluorophenyl)octane 

Relevant articles and documents

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Asymmetric Total Syntheses of Two Possible Diastereomers of Gliomasolide e and Its Structural Elucidation

The first total syntheses of two possible diastereomers of gliomasolide E, a 14-membered macrolides isolated from the marine sponge Phakellia fusca Thiele, which was collected from the South China Sea, is reported. Highlights of the synthesis include macrolactonization through intramolecular Horner-Wadsworth-Emmons olefination, Yamaguchi-Hirao alkynylation, and base-induced elimination reactions for propargyl alcohol synthesis as the key reactions. Detailed comparison of their 1H and 13C NMR (1D and 2D NMR data) and specific rotation with those of the natural product revealed that the absolute stereochemistry of gliomasolide E should be (2E,5R,7R,9R,13R).

Production of 2-Octenyl Radicals from the Fe(III)*Bleomycin-Mediated Fragmentation of 10-Hydroperoxy-8,12-octadecadienoic Acid

The Fe(III)*BLM-mediated fragmentation of 10-hydroperoxy-8,12-octadecadienoic acid was demonstrated unambiguously to occur via homolytic O-O bond scission.

CuBr2-catalyzed diastereoselective allylation: Total synthesis of decytospolides A and B and their C6-epimers

An efficient CuBr2-catalyzed diastereoselective allylation of a cyclic hemiacetal with allyltrimethylsilane as a nucleophile has been developed. The protocol offers a cost effective, protecting group tolerant, and operationally simple approach to 2,6-trans-disubstituted tetrahydropyran with excellent diastereoselectivity. Furthermore, the application of this methodology has been demonstrated in the total synthesis of decytospolides A and B and their C6-epimers.

Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12

An efficient synthesis of 15-deoxy-Δ12,14-prostaglandin J2 (15d-PGJ2, 1) is reported. The route described allows for diversification of the parent structure to prepare seven analogues of 1 in which the positioning of electrophilic sites is varied. These analogues were tested in SAR studies for their ability to reduce the secretion of proinflammatory cytokines. It was shown that the endocyclic enone is crucial for the bioactivity investigated and that the conjugated ω-side chain serves in a reinforcing manner.