cis-Nerolidol

Base Information

• Chemical Name: cis-Nerolidol
• CAS No.: 3790-78-1
• Deprecated CAS: 24163-92-6,53991-23-4
• Molecular Formula: C15H26 O
• Molecular Weight: 222.371
• Hs Code.: 2905290000
• European Community (EC) Number: 205-540-2,223-263-5
• UNII: 81K23DEF7B
• DSSTox Substance ID: DTXSID1047239
• Nikkaji Number: J217.684J
• Wikipedia: Nerolidol
• Wikidata: Q27269256
• Metabolomics Workbench ID: 130639
• ChEMBL ID: CHEMBL3185053
• Mol file: 3790-78-1.mol

Synonyms:3,7,11-trimethyl-1,6,10-dodecatrien-3-ol;nerolidol;nerolidol, (E)-isomer;nerolidol, (S-(E))-isomer;nerolidol, (S-(Z))-isomer;nerolidol, (Z)-isomer;peruviol

Chemical Property of cis-Nerolidol

Chemical Property:

• Refractive Index: n20/D 1.478(lit.)
• Boiling Point: 276°Cat760mmHg
• Flash Point: 109.9°C
• PSA: 20.23000
• Density: 0.869g/cm³
• LogP: 4.39630
• Storage Temp.: 2-8°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 269

Purity/Quality:

98% ^*data from raw suppliers

cis-Nerolidol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(C)(C=C)O)C)C
• Isomeric SMILES: CC(=CCC/C(=C\CCC(C)(C=C)O)/C)C
• 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.

Technology Process of cis-Nerolidol

There total 26 articles about cis-Nerolidol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(2S,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-3-iodomethyl-2-methyl-oxirane (85431-78-3) → (R)-(-)-trans-nerolidol (142-50-7,1119-38-6,2211-29-2,3790-78-1,7212-44-4,17430-12-5,35944-21-9,40716-66-3,53991-23-4,77171-59-6,132958-73-7,77551-75-8)

Guidance literature:

With zinc; In diethyl ether; acetic acid; for 1h; Ambient temperature;

DOI:10.1016/0040-4039(82)80144-5

Reference yield: 96.5%

sec.-butyl orthovanadate + (2Z,6Z)-farnesol (16106-95-9) + ethylene glycol (107-21-1) → cis-nerolidol (3790-78-1)

Guidance literature:

Reference yield: 95.0%

→ cis-nerolidol (3790-78-1)

Guidance literature:

upstream raw materials:

(Z)-nerylacetone

vinyl magnesium bromide

prenyl bromide

(6Z)-3,7,11-trimethyl-6,10-dodecadien-1-yn-3-ol

Downstream raw materials:

(E,Z)-α-farnesene

(Z)-beta-Farnesene

(Z,Z)-α-farnesene

bisabolol

Refernces

• 1、 Zhang, Qi,Tiefenbacher, Konrad. "Sesquiterpene Cyclizations inside the Hexameric Resorcinarene Capsule: Total Synthesis of δ-Selinene and Mechanistic Studies". supporting information. p. 12688 - 12695. Retrieved 2019/08/12.
• 2、 Nestl, Bettina M.,Geinitz, Christopher,Popa, Stephanie,Rizek, Sari,Haselbeck, Robert J.,Stephen, Rosary,Noble, Michael A.,Fischer, Max-Philipp,Ralph, Erik C.,Hau, Hoi Ting,Man, Henry,Omar, Muhiadin,Turkenburg, Johan P,Van Dien, Stephen,Culler, Stephanie J.,Grogan, Gideon,Hauer, Bernhard. "Structural and functional insights into asymmetric enzymatic dehydration of alkenols". . p. 275 - 281. Retrieved 2017/02/23.