1113-21-9

Basic information

• Product Name: Geranyl linalool
• Synonyms: T-Geranyl Linalool;Geranyl linalool, tech., ca. 95%;3,7,11,15-TETRAMETHYL-1,6,10,14-HEXADECATETRAEN-3-OL;3,7,11,15-TETRAMETHYL-1,6,10,14-HEXADECATETRAENE-3-OL;GERANYL LINALOL;GERANYL LINALOOL;Geranyl linalool, tech., mixture of isomers, ca. 95%;1,6,10,14-Hexadecatetraen-3-ol, 3,7,11,15-tetramethyl-, (6E,10E)-
• CAS NO: 1113-21-9
• Molecular Formula: C₂₀H₃₄O
• Molecular Weight: 290.48
• EINECS: 214-201-8
• Product Categories: Biochemistry;Terpenes;Terpenes (Others);Acyclic;Alkenes;Building Blocks;Chemical Synthesis;Organic Building Blocks;Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1113-21-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 250 °C
• Flash Point: 160°C
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.885 g/mL at 20 °C(lit.)
• Vapor Pressure: 1.09E-07mmHg at 25°C
• Refractive Index: n20/D 1.490
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slig
• PKA: 14.40±0.29(Predicted)
• Water Solubility: insoluble
• BRN: 6713421
• CAS DataBase Reference: Geranyl linalool(CAS DataBase Reference)
• NIST Chemistry Reference: Geranyl linalool(1113-21-9)
• EPA Substance Registry System: Geranyl linalool(1113-21-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: MM0335000
• F: 10
• Hazardous Substances Data: 1113-21-9(Hazardous Substances Data)

Usage

Description

Geranyl linalool is a diterpene alcohol, a colorless and transparent liquid, and a bioactive natural product. It is a straight chain diterpenoid and serves as an essential ingredient in determining the spice type. Geranyl linalool is also an important intermediate for Teprenone, a gastric mucosa protective agent.

Uses

Used in Fragrance Industry:
Geranyl linalool is used as a fragrant ingredient for its pleasant aroma.
Used in Insect Control:
Geranyl linalool is used as an insect pheromone and natural insecticide, imparting insecticidal properties to xylophagous insects and pine wood.
Used in Pharmaceutical Industry:
Geranyl linalool is used as a starting material in the synthesis of Teprenone, a gastric mucosa protective agent. By reacting with acetylated Meldrum's acid, Teprenone can be obtained in a convenient one-step synthesis method.
Used in Microbial Research:
Geranyl linalool has been used in studying its influence on pyocyanin and Pseudomonas quinolone signal (PQS) production by Pseudomonas aeruginosa.
Used in Environmental Research:
Geranyl linalool has shown poor inhibitory activity against carotenoid synthesis in Synechococcus, which can be useful in understanding the ecological roles of these microorganisms.

InChI:InChI=1/C20H34O/c1-7-20(6,21)16-10-15-19(5)14-9-13-18(4)12-8-11-17(2)3/h7,11,13,15,21H,1,8-10,12,14,16H2,2-6H3/b18-13+,19-15+

Upstream product

• 6138-90-5 trans-geranyl bromide 
• 593-60-2 Vinyl bromide 
• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 21064-19-7 trans,trans,trans-1,5,9-trimethyl-1,5,9-cyclododecatriene 
• 63525-04-2 4,8-Dimethyl-1,12-dioxotrideca-4E,8E-diene 
• 3796-70-1 trans geranyl acetone 
• 59905-15-6 dehydronerolidol 
• 97344-88-2 isopentenylmagnesium bromide 
• 1119-38-6 (S)-(+)-nerolidol 
• 24034-73-9 Geranylgeraniol 
• 500996-28-1 geranylgeraniol-2,3-epoxide 
• 3536-96-7 vinylmagnesium chloride 
• 1826-67-1 vinyl magnesium bromide 
• 917-57-7 vinyllithium 

Downstream Products

• 50848-64-1 2E,6E,10E-geranylgeranyl bromide 
• 3796-63-2 (E,E,E)-geranylgeranylacetone 
• 80321-08-0 (2Z,6E,10E)-1-bromo-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene 
• 3796-64-3 (5Z,9E,13E)-2-acetyl-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one 
• 22488-05-7 geranylfarnesol 
• 57804-27-0 ((2E,6E,10E)-3,7,11,15-Tetramethyl-hexadeca-2,6,10,14-tetraenylsulfanyl)-benzene 
• 89503-43-5 3,7,15,19,23,27-hexamethyloctaeicosa-2Z,6Z,10E,14E,18E,22E,26-hepten-1-ol benzyl ester 
• 89503-41-3 11-hydroxymethyl-3,7,15,19,23,27-hexamethyloctaeicosa-2Z,6Z,10E,14E,18E,22E,26-hepten-1-ol benzyl ester 
• 89503-39-9 11-formyl-3,7,15,19,23,27-hexamethyloctaeicosa-2Z,6Z,10E,14E,18E,22E,26-hepten-1-ol benzyl ester 
• 89503-31-1 2-((4E,8E,12E)-5,9,13,17-Tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraenyl)-[1,3]dioxolane 
• 89503-44-6 3,7,11,15,19,23,27-heptamethyloctaeicosa-2E,6Z,10Z,14E,18E,22E,26-heptaen-1-ol benzyl ether 
• 89503-42-4 3,7,15,19,23,27-hexamethyl-11-hydroxymethyloctaeicosa-2E,6Z,10E,14E,18E,22E,26-heptaen-1-ol benzyl ether 
• 89503-40-2 benzyl 3,7,15,19,23,27-hexamethyl-11-formyloctaeicosa-2E,6Z,10E,14E,18E,22E,26-heptaen-1-ol 
• 540-05-6 all-(E)-phytofluene 

Relevant articles and documents

Synthesis method of teprenone and intermediate thereof

The invention relates to synthesis methods of teprenone and an intermediate thereof. The synthesis of the intermediate all-trans (5E,9E)-farnesyl acetone comprises: 1) in the presence of a catalyst, carrying out a carroll rearrangement reaction on the mixture of 5E-nerolidol and 5Z-nerolidol and hydrocarbonyl acetoacetate to obtain the isomer mixture of (5Z,9Z)-farnesyl acetone, (5Z,9E)-farnesyl acetone, (5E,9Z)-farnesyl acetone, and (5E,9E)-farnesyl acetone, wherein the content of (5E,9E)-farnesyl acetone in the isomer mixture is controlled at more than 18%; and 2) carrying out low-temperature crystallization separation on the isomer mixture in a moderately polar solvent to obtain the all-trans (5E,9E)-farnesyl acetone. According to the present invention, the high-purity all-trans (5E,9E)-farnesyl acetone is obtained by using the mixture of 5E-nerolidol and 5Z-nerolidol as the raw material through the low-temperature crystallization separation, such that the teprenone with the qualified quality can be conveniently obtained.

Process for synthesizing teprenone

The invention discloses a process for synthesizing teprenone.According to the process for synthesizing teprenone, nerolidol is adopted as an initial raw material and subjected to selenium dioxide and tert-butyl hydroperoxide oxidizing in sequence, nerolidol and dihydropyran are subjected to acid catalysis to form acetal, acetal reacts with a Grignard reagent on the presence of copper salt and reacts with methyl acetoacetate on the presence of aluminum salt, and the teprenone product consistent with the configuration of products sold on the market is obtained through four steps of reactions.According to a preparation method of teprenone, the raw material is cheap and easy to obtain, operation is easy and convenient, the reaction conditions are mild, and industrial production is expected to be achieved.