3790-78-1

Basic information

• Product Name: CIS-NEROLIDOL
• Synonyms: CIS-NEROLIDOL;CIS-3,7,11-TRIMETHYL-1,6,10-DODECATRIEN-3-OL;NEROLIDOL, CIS-;(Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol;(Z)-nerolidol,(6Z)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol,cis-nerolidol;NEROLIDOL, cis-(SG);CIS-NEROLIDOL WITH GC;(6Z)-3,7,11-Trimethyl-1,6,10-dodecatriene-3-ol
• CAS NO: 3790-78-1
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.37
• EINECS: 205-540-2
• Mol File: 3790-78-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 70 °C0.1 mm Hg(lit.)
• Flash Point: 96℃
• Appearance: /
• Density: 0.876 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.478(lit.)
• Storage Temp.: 2-8°C
• BRN: 1724137
• CAS DataBase Reference: CIS-NEROLIDOL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-NEROLIDOL(3790-78-1)
• EPA Substance Registry System: CIS-NEROLIDOL(3790-78-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• Hazardous Substances Data: 3790-78-1(Hazardous Substances Data)

Usage

Uses

cis-Nerolidol is one of the main component in the essential oils from fresh aerial parts of Thymus ciliatus (Lamiaceae). Also, it is a terpene that displays high potency on the contractility of cardiac muscle in guinea pig left atrium. A potential and effective treatment for malaria.

Purification Methods

1 2 2o/3mm, d 4 0.73, n D 1.477, [cis 3790-78-1] b 70o/0.1mm, [trans 40716-66-3] b 78o/0.2mm, 145-146o/2mm. Purify it by TLC on plates of Kieselguhr G [McSweeney J Chromatogr 17 183 1965] or silica gel impregnated with AgNO3, using 1,2-CH2Cl2/CHCl3/EtOAc/PrOH (10:10:1:1) as solvent system. Also by GLC on butanediol succinate (20%) on Chromosorb W. Stored it under N2 at ~5o in the dark. [Beilstein 1 IV 2336.]

InChI:InChI=1/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11-

Upstream product

• 3879-26-3 (Z)-nerylacetone 
• 1826-67-1 vinyl magnesium bromide 
• 17958-05-3 (6Z)-3,7,11-trimethyl-6,10-dodecadien-1-yn-3-ol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 16106-95-9 (2Z,6Z)-farnesol 
• 107-21-1 ethylene glycol 
• 372-97-4 farnesyl pyrophosphate 
• 40716-67-4 (3RS)-nerolidyl diphosphate 
• 132407-52-4 tert-Butyl-((E)-(R)-6-chloro-1,5-dimethyl-1-vinyl-hex-4-enyloxy)-dimethyl-silane 
• 132407-51-3 (E)-(R)-6-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,7-dien-1-ol 
• 132407-50-2 (R)-tert-butyl((3,7-dimethylocta-1,6-dien-3-yl)oxy)dimethylsilane 
• 126-91-0 linalool 
• 85505-95-9 (2R,3R)-3-((E)-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl-methanol 
• 85431-77-2 Toluene-4-sulfonic acid (2R,3S)-3-((E)-4,8-dimethyl-nona-3,7-dienyl)-3-methyl-oxiranylmethyl ester 

Downstream Products

• 502-61-4 (E,Z)-α-farnesene 
• 28973-97-9 (Z)-beta-Farnesene 
• 28973-99-1 (Z,Z)-α-farnesene 
• 515-69-5 bisabolol 
• 80767-67-5 alpha-bisabolyl formate 
• 626-96-0 4-oxopentanal 
• 67-64-1 acetone 
• 59403-81-5 β-snyderol 
• 59403-83-7 α-snyderol 
• 18794-84-8 7,11-dimethyl-3-methylene-1,6,10-dodecatriene 
• 495-62-5 (Z)-γ-bisabolene 
• 502-67-0 Farnesal 
• 4380-32-9 (2Z,6E)-farnesal 
• 564-20-5 (3aR)-(+)-sclareolide 

Relevant articles and documents

Method for efficiently preparing enol through selective hydrogenation of alkynol

The invention provides a method for efficiently preparing enol through selective hydrogenation of alkynol. A conventional tank reactor and a micro-channel reactor are combined for use, and the micro-channel reactor can be used for quickly preparing an enol product after immobilizing a rare earth metal doped catalyst, so that the reaction time is shortened, and the production efficiency is improved. And a phosphine compound is added as a side reaction inhibitor to improve the selectivity.

Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum

A newly identified bacterial (Z)-γ-bisabolene synthase was used for investigating the cyclisation mechanism of the sesquiterpene. Since the stereoinformation of both chiral putative intermediates, nerolidyl diphosphate (NPP) and the bisabolyl cation, is lost during formation of the achiral product, the intriguing question of their absolute configurations was addressed by incubating both enantiomers of NPP with the recombinant enzyme, which resolved in an exclusive cyclisation of (R)-NPP, while (S)-NPP that is non-natural to the (Z)-γ-bisabolene synthase was specifically converted into (E)-β-farnesene. A hypothetical enzyme mechanistic model that explains these observations is presented.

Isotope sensitive branching and kinetic isotope effects to analyse multiproduct terpenoid synthases from Zea mays

Multiproduct terpene synthases TPS4-B73 and TPS5-Delprim from Zea mays exhibit isotopically sensitive branching in the formation of mono- and sesquiterpene volatiles. The impact of the kinetic isotope effects and the stabilization of the reactive intermediates by hyperconjugation along with the shift of products from alkenes to alcohols are discussed.