delta-Cadinol

Base Information

• Chemical Name: delta-Cadinol
• CAS No.: 19435-97-3
• Molecular Formula: C15H26O
• Molecular Weight: 222.371
• DSSTox Substance ID: DTXSID00173061
• Nikkaji Number: J15.509H
• Wikipedia: Delta-Cadinol
• Wikidata: Q5254530
• Mol file: 19435-97-3.mol

Synonyms:delta-Cadinol;19435-97-3;Torreyol;1-Naphthalenol, 1,2,3,4,4a,7,8,8a-octahydro-1,6-dimethyl-4-(1-methylethyl)-, (1R-(1alpha,4beta,4abeta,8abeta))-;1.beta.-Cadin-4-en-10-ol;Muurolol;SCHEMBL5653564;DTXSID00173061;CHEBI:156223;LHYHMMRYTDARSZ-ZQDZILKHSA-N;1-Naphthalenol, 1,2,3,4,4a,7,8,8a-octahydro-1,6-dimethyl-4-(1-methylethyl)-, [1R-(1.alpha.,4.beta.,4a.beta.,8a.beta.)]-;Q5254530;(1R,4S,4aR,8aS)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol

Chemical Property of delta-Cadinol

Chemical Property:

• Vapor Pressure: 8.96E-05mmHg at 25°C
• Boiling Point: 303.4°Cat760mmHg
• Flash Point: 128.3°C
• Density: 0.937g/cm³
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 292

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2C(CCC(C2CC1)(C)O)C(C)C
• Isomeric SMILES: CC1=C[C@H]2[C@@H](CC[C@@]([C@H]2CC1)(C)O)C(C)C

Technology Process of delta-Cadinol

There total 32 articles about delta-Cadinol 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: 71.0%

C22H34N2O3S (94853-23-3) → (±)-torreyol (481-34-5,5937-11-1,19435-97-3,19912-62-0,39864-11-4,43060-37-3,58560-29-5,58580-31-7,65700-78-9,71300-63-5,81967-90-0,95342-27-1,106035-59-0,133645-25-7)

Guidance literature:

With sodium methylate; In diethylene glycol dimethyl ether; at 160 ℃; for 2.5h;

DOI:10.1016/S0040-4020(01)91500-5

Reference yield: 55.0%

C14H22O + methylmagnesium bromide (75-16-1) → (±)-torreyol (481-34-5,5937-11-1,19435-97-3,19912-62-0,39864-11-4,43060-37-3,58560-29-5,58580-31-7,65700-78-9,71300-63-5,81967-90-0,95342-27-1,106035-59-0,133645-25-7) + (±)-cedrelanol (481-34-5,5937-11-1,19435-97-3,19912-62-0,39864-11-4,43060-37-3,58560-29-5,58580-31-7,65700-78-9,71300-63-5,81967-90-0,95342-27-1,106035-59-0,133645-25-7)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.7b00013

Reference yield: 55.0%

C14H22O + methylmagnesium bromide (75-16-1) → (±)-torreyol (481-34-5,5937-11-1,19435-97-3,19912-62-0,39864-11-4,43060-37-3,58560-29-5,58580-31-7,65700-78-9,71300-63-5,81967-90-0,95342-27-1,106035-59-0,133645-25-7) + (±)-cedrelanol (481-34-5,5937-11-1,19435-97-3,19912-62-0,39864-11-4,43060-37-3,58560-29-5,58580-31-7,65700-78-9,71300-63-5,81967-90-0,95342-27-1,106035-59-0,133645-25-7)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.7b00013

upstream raw materials:

formic acid

(-)-germacra-1(10),5(E)-dien-4β-ol

α-cadinol formate

farnesyl pyrophosphate

Downstream raw materials:

α-cadinol p-nitrobenzoate

Amorphan-4α.9β-diol

Cadinan-4-on-9β-ol

Amorphan-4-on-9β-ol

Refernces

• 1、 Lauchli, Ryan,Pitzer, Julia,Kitto, Rebekah Z.,Kalbarczyk, Karolina Z.,Rabe, Kersten S.. "Improved selectivity of an engineered multi-product terpene synthase". supporting information. p. 4013 - 4020. Retrieved 2014/06/09.
• 2、 Nordin,Hedenstrom,Hogberg. "Stereochemistry of 1,6-germacradien-5-ol, a constituent of the needles of Scots pine (Pinus sylvestris) and of the defence secretion from larvae of the pine sawfly Neodiprion sertifer". . p. 124 - 132. Retrieved 2007/10/03.