1117-52-8

Basic information

• Product Name: (5E,9E)-6,10,14-Trimethylpentadeca-5,9,13-trien-2-one
• Synonyms: FARNEZYLACETONE;FEMA 3442;(5E,9E)-6,10,14-Trimethylpentadeca-5,9,13-trien-2-one;(5E,9E)-6,10,14-Trimethyl-5,9,13-pentadecatrien-2-one;5,9,13-Pentadecatrien-2-one, 6,10,14-trimethyl-, (E,E)-;(E,E)-6,10,14-trimethylpentadeca-5,9,13-trien-2-one;(E,E)-farnesylacetone,(5E,9E)-6,10,14-trimethyl-5,9,13-pentadecatrien-2-one,farnesylacetone,;Farnesylaceton
• CAS NO: 1117-52-8
• Molecular Formula: C₁₈H₃₀O
• Molecular Weight: 262.43
• EINECS: 212-097-9
• Product Categories: Cnbio
• Mol File: 1117-52-8.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 372.773 °C at 760 mmHg
• Flash Point: 140.43 °C
• Appearance: /
• Density: 0.88 g/mL at 20 °C(lit.)
• Vapor Pressure: 9.39E-06mmHg at 25°C
• Refractive Index: n20/D 1.481
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly)
• Stability: Light Sensitive
• CAS DataBase Reference: (5E,9E)-6,10,14-Trimethylpentadeca-5,9,13-trien-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5E,9E)-6,10,14-Trimethylpentadeca-5,9,13-trien-2-one(1117-52-8)
• EPA Substance Registry System: (5E,9E)-6,10,14-Trimethylpentadeca-5,9,13-trien-2-one(1117-52-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• Hazardous Substances Data: 1117-52-8(Hazardous Substances Data)

Usage

Description

(5E,9E)-6,10,14-Trimethylpentadeca-5,9,13-trien-2-one, also known as E,E-Farnesylacetone, is a natural organic compound that belongs to the terpene ketone family. It is characterized by the presence of an (E,E)-farnesyl group bonded to one of the alpha-methyls of acetone. (5E,9E)-6,10,14-Trimethylpentadeca-5,9,13-trien-2-one is commonly found in many essential oils and has been studied for its potential biological activities.

Uses

Used in Pharmaceutical Industry:
(5E,9E)-6,10,14-Trimethylpentadeca-5,9,13-trien-2-one is used as a bioactive compound for its ability to inhibit electron transport in isolated rat liver mitochondria. This property suggests its potential use in the development of drugs targeting mitochondrial function and energy metabolism, which could have implications for the treatment of various diseases associated with mitochondrial dysfunction.
Used in Essential Oils Industry:
(5E,9E)-6,10,14-Trimethylpentadeca-5,9,13-trien-2-one is used as a key component in many essential oils, contributing to their characteristic fragrances and properties. Its presence in essential oils may also contribute to their potential therapeutic effects, such as antimicrobial, anti-inflammatory, and antioxidant activities, depending on the specific oil in which it is found.

InChI:InChI=1/C18H30O/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19/h9,11,13H,6-8,10,12,14H2,1-5H3/b16-11+,17-13+

Upstream product

• 3796-70-1 trans geranyl acetone 
• 1066-26-8 sodium acetylide 
• 917-64-6 methyl magnesium iodide 
• 5981-31-7 1-cyano-4,8,12-trimethyl-3E,7E,11-tridecatriene 
• 63525-04-2 4,8-Dimethyl-1,12-dioxotrideca-4E,8E-diene 
• 1530-33-2 isopropyltriphenylphosphonium bromide 
• 51921-98-3 (4E,8E)-ethyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate 
• 140176-36-9 (10E)-13-bromo-2,6,10-trimethyltrideca-2,6,10-triene 
• 108-24-7 acetic anhydride 
• 6784-45-8 (2E,6E)-farnesyl chloride 
• 105-45-3 acetoacetic acid methyl ester 
• 24163-93-7 farnesyl bromide 
• 141-97-9 ethyl acetoacetate 
• 80868-09-3 (5E,9E)-6,10,14-Trimethyl-3-(toluene-4-sulfonyl)-pentadeca-5,9,13-trien-2-one 

Downstream Products

• 3796-64-3 (5Z,9E,13E)-2-acetyl-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one 
• 3796-63-2 (E,E,E)-geranylgeranylacetone 
• 502-69-2 6,10,14-Trimethyl-2-pentadecanon 
• 1027-71-0 sclareoloxide 
• 1113-21-9 (6E,10E)-geranyllinalool 
• 947587-73-7 C₂₇H₄₀O₃ 
• 947688-20-2 C₂₉H₄₄O₃ 
• 505-32-8 isophytol 
• 13920-11-1 2E,6E,10E-geranylgeranyl aldehyde 
• 50848-64-1 2E,6E,10E-geranylgeranyl bromide 
• 10154-05-9 Methyl 4-trans-8-trans-farnesylacetat 
• 79491-08-0 dimethyl 2-(3,7,11-trimethyldodeca-2,6,10-trienyl)malonate 
• 22076-59-1 11',12'-dihydrospheroidene 
• 22076-59-1 (6E,10E,14E,16E,18E,20E,22E,24Z,26E,28E)-31-Methoxy-2,6,10,14,19,23,27,31-octamethyl-dotriaconta-2,6,10,14,16,18,20,22,24,26,28-undecaene 

Relevant articles and documents

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Biosynthesis of indole diterpenes, emindole, and paxilline: Involvement of a common intermediate

The key step for construction of the carbon skeleton in the indole diterpenes, paxilline, and emindole DA was examined. Intact incorporation of multiply 2H-labeled 3-geranylgeranylindole into two different fungal metabolites proves 3-geranylgeranylindole to be a biosynthetic intermediate. These results give evidence that indole diterpenes are biosynthesized via epoxidation of a common intermediate, and the subsequent cationic cyclization, analogous to those in the steroid biosynthesis.

Preparation method of vitamin A and vitamin A ester

The invention provides a novel method for preparing vitamin A and vitamin A ester with farnesene as a raw material. The method comprises the following steps: reacting farnesene with acetoacetate underthe action of a catalyst to obtain farnesyl keto ester; carrying out a cyclization reaction and a dehydrogenation reaction on farnesene acetone, and then reacting a reaction product with vinyl magnesium halide to generate vinyl alcohol; carrying out a rearrangement reaction on vinyl alcohol to obtain vitamin A; and subjecting the vitamin A to an esterification reaction to obtain the vitamin A ester. The method avoids the defects of the existing processes, and the process line of the method is economical and effective.

SYNTHESIS OF ALKYL 2-ACETYL-5,9,13-TRIMETHYLTETRADECA-4,8,12-TRIENOATES AND DERIVATIVES BY A NON-CONTINUOUS PRODUCTION PROCESS

The present invention relates to the manufacturing of a process of alkyl 2- acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoates and alkyl 2-acetyl-9,13-di- methyl-5-methylenetetradeca-8,12-dienoate as well as 6,10,14-trimethylpenta- deca-5,9,13-trien-2-one and 10,14-dimethyl-6-methylenepentadeca-9,13-dien-2-5 one and 6,10,14-trimethylpentadecan-2-one.

GGA DERIVATIVES

This invention relates to geranylgeranyl acetone (GGA) derivatives, pharmaceutical compositions comprising GGA derivatives and the use of GGA derivatives.