trans-Nerolidol

Base Information

• Chemical Name: trans-Nerolidol
• CAS No.: 7212-44-4
• Deprecated CAS: 35944-21-9
• Molecular Formula: C15H26O
• Molecular Weight: 222.371
• Hs Code.: 2905.22 DERIVATION
• 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: 7212-44-4.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:

• Appearance/Colour: Clear slightly yellow liquid
• Vapor Pressure: 0.000616mmHg at 25°C
• Melting Point: -75 °C
• Refractive Index: n20/D 1.479(lit.)
• Boiling Point: 275.999 °C at 760 mmHg
• PKA: 14.44±0.29(Predicted)
• Flash Point: 109.916 °C
• PSA: 20.23000
• Density: 0.87 g/cm³
• LogP: 4.39630
• Storage Temp.: 2-8°C
• Solubility.: 0.014g/l
• Water Solubility.: immiscible
• 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(Mixtureofcisandtrans,Stablizedwithα-tocopherol) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-36-61-60

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: Nerolidol occurs naturally including the essential oil of neroli, ylang-ylang, and Peru balsam. It has a faint, fresh, unusually sweet, tenacious, floral odor similar to rose and apple. It can be used as a flavor ingredient in foods, such as baked goods, frozen dairy, nonalcoholic beverages, and soft candy. It is also used as fragrance in the perfumery. Nerolidol has a faint, floral odor similar to rose and apple. It is an unusually sweet, fresh, tenacious odor. The natural product can be dextro- or levo-rotatory, whereas the synthetic product is optically inactive; the double bond at positions 6-7 accounts for the cis- and trans-forms.
• Uses: 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. anti-ulcer, insect antifeedant

Technology Process of trans-Nerolidol

There total 22 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: 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: 55.0%

(2R,3R)-3-((E)-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl-methanol (85505-95-9) → (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:

(2R,3R)-3-((E)-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl-methanol; With pyridine; iodine; triphenylphosphine; In diethyl ether; acetonitrile; at 0 ℃; for 2h; Inert atmosphere;

With water; In diethyl ether; acetonitrile; for 12h; Reflux;

DOI:10.3762/bjoc.15.75

Reference yield: 8.0%

farnesol (4602-84-0) → (+/-)-nerolidol (7212-44-4)

Guidance literature:

With PDS; PS-TEMPO; Ag-Al₂O₃; In water; toluene; at 80 ℃; for 2.5h; Product distribution / selectivity;

upstream raw materials:

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

diethyl ether

pseudo-ionone

farnesol

Downstream raw materials:

farnesal

cis-α-farnesene

farnesyl bromide

bisabolol

Refernces

• 1、 De Meireles, Augusto L.P.,Costa, Maíra Dos Santos,Da Silva Rocha, Kelly A.,Gusevskaya, Elena V.. "Heteropoly acid catalyzed cyclization of nerolidol and farnesol: Synthesis of α-bisabolol". . p. 271 - 275. Retrieved 2015/07/07.
• 2、 Kodama, Takeshi,Aoki, Shingo,Matsuo, Tomoki,Tachi, Yoshimitsu,Nishikawa, Keisuke,Morimoto, Yoshiki. "Biomimetic total synthesis of (-)-neroplofurol and (+)-ekeberin D4triggered by hydrolysis of terminal epoxides". . p. 1662 - 1664. Retrieved 2015/02/19.