167820-65-7

Basic information

• Product Name: (6Z)-nona-3,6-dien-1-ol
• Synonyms: (6Z)-Nona-3,6-dien-1-ol; 3,6-nonadien-1-ol, (6Z)-
• CAS NO: 167820-65-7
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22
• Mol File: 167820-65-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 214.7°C at 760 mmHg
• Flash Point: 84.6°C
• Density: 0.866g/cm³
• Vapor Pressure: 0.0336mmHg at 25°C
• Refractive Index: 1.472
• CAS DataBase Reference: (6Z)-nona-3,6-dien-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (6Z)-nona-3,6-dien-1-ol(167820-65-7)
• EPA Substance Registry System: (6Z)-nona-3,6-dien-1-ol(167820-65-7)

Safety Data

• Hazardous Substances Data: 167820-65-7(Hazardous Substances Data)

Usage

Description

(6Z)-nona-3,6-dien-1-ol, with the molecular formula C9H16O, is an unsaturated alcohol characterized by a chain of nine carbon atoms, featuring a double bond at the 6th carbon and a hydroxyl group at the first carbon. This organic compound is known for its fruity and floral scent, making it a valuable component in the flavor and fragrance industry. Moreover, its chemical properties allow it to serve as a versatile intermediate in the synthesis of other organic compounds. Interestingly, it also finds application in pest control as a pheromone, particularly for attracting the Mediterranean fruit fly.

Uses

Used in Flavor and Fragrance Industry:
(6Z)-nona-3,6-dien-1-ol is used as a key component in the creation of various fragrances and flavors due to its distinctive fruity and floral scent. This application takes advantage of the compound's natural aroma to enhance the sensory experience of consumer products.
Used as a Chemical Intermediate:
In the realm of organic chemistry, (6Z)-nona-3,6-dien-1-ol serves as a valuable intermediate in the synthesis of other complex organic compounds. Its unique structure facilitates chemical reactions that lead to the production of a wide range of products, showcasing its utility in the chemical industry.
Used in Pest Control:
(6Z)-nona-3,6-dien-1-ol is employed as a pheromone in the field of pest control, specifically as an attractant for the Mediterranean fruit fly. By mimicking the natural chemical signals used by these insects, this compound can be used to lure and control their populations, providing an effective and environmentally friendly approach to pest management.

Upstream product

• 1638153-00-0 (3Z,6Z)-9,9-dimethoxy-nona-3,6-dien-1-yl 4-methylbenzenesulfonate 
• 696-86-6 cis,cis,cis-1,4,7-cyclononatriene 
• 1638152-99-4 (3Z,6Z)-9,9-dimethoxynona-3,6-dien-1-ol 
• 144647-88-1 [(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-hex-3-enyl]-triphenyl-phosphonium; bromide 
• 144460-30-0 ((Z)-6-Bromo-hex-3-enyloxy)-tert-butyl-diphenyl-silane 
• 16400-32-1 1-bromo-pent-2-yne 
• 81812-26-2 (Z,Z)-1,1-diethoxynona-3,6-diene 
• 6789-80-6 (3Z)-hexenal 
• 928-96-1 (Z)-3-Hexen-1-ol 
• 92666-05-2 toluene-4-sulfonic acid pent-2-ynyl ester 
• 6261-22-9 pent-2-yn-1-ol 
• 21944-83-2 (3Z,6Z)-nona-3,6-dienal 
• 144460-31-1 tert-Butyl-[((3Z,6Z)-nona-3,6-dienyl)oxy]-diphenyl-silane 
• 57386-91-1 nona-3,6-diyn-1-ol 

Downstream Products

• 26370-28-5 cis-3,cis-6-nonadienol 
• 118492-81-2 8(S)-hydroxy-(5Z,9E,11Z,14Z,17Z)-eicosapentaenoic acid 
• 163041-94-9 (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate 
• 169392-17-0 (4Z,7Z)-4,7-decadienoic acid 
• 75207-09-9 LTC5 
• 79695-13-9 LTD5 
• 79695-14-0 LTE5 
• 90121-06-5 4-[((1E,3E,5Z,8Z,11Z)-3-Tetradeca-1,3,5,8,11-pentaenyl)-oxiranyl]-butyric acid methyl ester 
• 81926-94-5 all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate 
• 90121-03-2 (3Z,6Z)-1-bromonona-3,6-diene 

Relevant articles and documents

Direct preparation of (Z,Z)-1,4-dienic units with a new C6 homologating agent: Synthesis of α-linolenic acid

Syntheses of two C6 homologating agents 2a and 2f are described. These agents allow direct access to the (Z,Z)-1,4-diene unit 3, a moiety present in a wide number of natural compounds. Compound 2a is prepared in 40% overall yield by selective epoxidation of methoxycyclohexa-1,4-diene followed by oxidative ring cleavage and transatalization. Compound 2f is obtained in 90% yield by a one-step oxidative dimerization of phosphonium salt 1. A short synthetic application of these two new C6 homologating agents to the synthesis of α-linolenic acid is described.

Pheromone synthesis. Part 257: Synthesis of methyl (2E,4Z,7Z)-2,4,7-decatrienoate and methyl (E)-2,4,5-tetradecatrienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)

Tandem Dess-Martin oxidation/Wittig reaction of (2Z,5Z)-2,5-octadien-1-ol yielded methyl (2E,4Z,7Z)-2,4,7-decatrienoate, a newly discovered pheromone component of the male dried bean beetle, while that of (±)-2,3-dodecadien-1-ol gave (±)-methyl (E)-2,4,5-tetradecatrienoate, the racemate of the known and major pheromone component. Methyl (2E,4E,7Z)-2,4,7-decatrienoate was also synthesized, which is the methyl ester of an acid metabolite of a green alga. Reduction of 2,5-octadiyn-1-ol with Zn-Cu/EtOH cleanly gave (2Z,5Z)-2,5-octadien-1-ol.

Total synthesis and bioactivities of two proposed structures of maresin

Maresin is a potent anti-inflammatory lipid mediator derived from docosahexaenoic acid (DHA). A highly convergent total synthesis of two proposed structures of C7-epimeric maresins from the four known fragments was achieved in 17 steps. The three key coupling reactions were the BF3-mediated alkyne attack on the epoxide, chiral titanium complex-promoted enantioselective alkyne addition to the aldehyde, and a Julia-Kocienski olefination. The two synthesized diastereomers were found to be comparably active in blocking neutrophil infiltration in the acute peritonitis model. Copyright