trans-Nerolidol

Base Information

• Chemical Name: trans-Nerolidol
• CAS No.: 40716-66-3
• Deprecated CAS: 35944-21-9
• Molecular Formula: C15H26O
• Molecular Weight: 222.371
• Hs Code.: 2905290000
• European Community (EC) Number: 230-597-5,205-540-2,255-053-4
• UNII: FG5V0N8P2H
• DSSTox Substance ID: DTXSID2040783
• Nikkaji Number: J26.204H,J8.909E
• Wikipedia: Nerolidol
• Wikidata: Q415421
• ChEMBL ID: CHEMBL25424
• Mol file: 40716-66-3.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 trans-Nerolidol

Chemical Property:

• Refractive Index: n20/D 1.479(lit.)
• Boiling Point: 114oC (1 mmHg)
• PKA: 14.40±0.29(Predicted)
• Flash Point: 96 ºC
• PSA: 20.23000
• Density: 0.875
• LogP: 4.39630
• Storage Temp.: ?20°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:

99.9% ^*data from raw suppliers

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
• Description: trans-Nerolidol is a sesquiterpene that has been found in various plants, including C. sativa, and has diverse biological activities, including antimicrobial, antioxidant, anticancer, and insecticidal properties. In a disc assay, trans-nerolidol inhibits the growth of S. aureus, B. subtilis, E. coli, and S. cerevisiae with zones of inhibition measuring 10, 9, 10, and 4 mm, respectively. It reduces viability of CaCo-2 adenocarcinoma cells with an IC50 value of 28.7 mg/L and reduces production of reactive oxygen species (ROS). trans-Nerolidol is insecticidal against A. aegypti larvae with a 24-hour LC50 value of 9 mg/L.

Technology Process of trans-Nerolidol

There total 42 articles about trans-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: 96.0%

(bicyclo<2.2.1>heptene-5 yle-2)-1 trimethyl-1,5,9 decatriene-4,8 ol-1 (86361-09-3) → (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (40716-66-3)

Guidance literature:

at 550 ℃; under 0.01 Torr;

DOI:10.1016/S0040-4020(01)91839-3

Reference yield: 93.0%

(+/-)-cis-nerolidyl-THP (958637-81-5) → (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (40716-66-3)

Guidance literature:

bis(trimethylsilyl)sulphate; In methanol; 1,2-dichloro-ethane; for 0.166667h; Ambient temperature;

DOI:10.1055/s-1981-29640

Reference yield: 87.0%

trans geranyl acetone (3796-70-1) + vinyl magnesium bromide (1826-67-1) → (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (40716-66-3)

Guidance literature:

In dichloromethane; 1.) 0 deg C, 15 min, 2.) room temperature, 3 h;

DOI:10.1021/ja00394a032

upstream raw materials:

trans geranyl acetone

vinyl magnesium bromide

prenyl bromide

dehydronerolidol

Downstream raw materials:

2,6,10-trimethyldodecane

(E)-β-farnesene

(E,E)-alpha-farnesene

α-bisabolene

Refernces

• 1、 Rinkel, Jan,Dickschat, Jeroen S.. "Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum". supporting information. p. 789 - 794. Retrieved 2019/04/17.
• 2、 Mao, Shanjun,Zhao, Bowen,Wang, Zhe,Gong, Yutong,Lü, Guofeng,Ma, Xiao,Yu, Lili,Wang, Yong. "Tuning the catalytic performance for the semi-hydrogenation of alkynols by selectively poisoning the active sites of Pd catalysts". . p. 4143 - 4151. Retrieved 2019/08/07.