Cedrol

Base Information

• Chemical Name: Cedrol
• CAS No.: 77-53-2
• Deprecated CAS: 13567-37-8
• Molecular Formula: C15H26O
• Molecular Weight: 222.371
• Hs Code.: 29062990
• European Community (EC) Number: 201-035-6
• NSC Number: 403883,46153
• UNII: 63ZM9703BO
• DSSTox Substance ID: DTXSID1041269
• Nikkaji Number: J499.451E
• Wikipedia: Cedrol
• Wikidata: Q1052617
• RXCUI: 1670019
• Metabolomics Workbench ID: 28417
• ChEMBL ID: CHEMBL1974890
• Mol file: 77-53-2.mol

Synonyms:8-epicedrol;cedrol

Chemical Property of Cedrol

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 55-59 °C(lit.)
• Refractive Index: 1.519
• Boiling Point: 277.2 °C at 760 mmHg
• PKA: 15.35±0.60(Predicted)
• Flash Point: 115.5 °C
• PSA: 20.23000
• Density: 1 g/cm³
• LogP: 3.60980
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (10 mg/ml)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 321

Purity/Quality:

99% ^*data from raw suppliers

(+)-Cedrol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C13CCC(C(C3)C2(C)C)(C)O
• Isomeric SMILES: C[C@@H]1CC[C@@H]2[C@]13CC[C@@]([C@H](C3)C2(C)C)(C)O
• Description: Cedrol is a sesquiterpene alcohol found in conifers mainly of the genera Cupressus, Juniperus, and Cedrus. It has been found to possess significant anticancer activity against glioblastoma in vitro and in vivo via cell growth inhibition, ROS generation, and DNA damage.1 Cedrol also displayed synergistic effects with temozolomide against glioblastoma in vitro and in vivo via reduced expression of drug resistance proteins.1,2 Cedrol inhibited the growth of human renal adenocarcinoma and amelanotic melanoma cells3 and induced autophagy and apoptosis in A549 non-small cell lung carcinoma cells4.
• Uses: acaricide, enhances skin ECM production (+)-Cedrol can be used as a starting material for the preparation of cedryl acetate by acetylation using acetic anhydride in the presence of an acid catalyst. It can also be incorporated as a precursor for the total synthesis of rare illicium sesquiterpene (+)-pseudoanisatin via selective C-H bond functionalization.

Technology Process of Cedrol

There total 19 articles about Cedrol 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:

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → β‐cedrene (546-28-1) + (+)-cedrol (77-53-2) + alpha-cedrene (469-61-4) + (-)-(3R,3aS,6S,7R,8aS)-isocedrol (19903-73-2)

Guidance literature:

With epicedrol synthase; In aq. buffer; at 30 ℃; for 1h; pH=8.5; Enzymatic reaction;

DOI:10.1016/j.tetlet.2016.01.109

Reference yield:

3-Norcedr-2-en-3-on (40768-85-2,109312-44-9) → (+)-cedrol (77-53-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-C / ethanol

2: diethyl ether / Heating

With hydrogen; palladium on activated charcoal; In diethyl ether; ethanol;

DOI:10.1021/ja01475a030

Reference yield:

(3aR)-2c-acetyl-1,1,4c-trimethyl-(6ac)-hexahydro-pentalene-3ar-carboxylic acid methyl ester (76679-86-2,101262-59-3) → (+)-cedrol (77-53-2)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) LiAlH₄, (ii) CrO₃, Py, (iii) aq. KOH

2: H₂ / Pd-C / ethanol

3: diethyl ether / Heating

With hydrogen; palladium on activated charcoal; In diethyl ether; ethanol;

DOI:10.1021/ja01475a030

upstream raw materials:

methyllithium

15-nor-3-oxo cedrane

3-Nor-cedrol

3-Norcedr-2-en-3-on

Downstream raw materials:

(-)-α-cedrene

(8aS)-6c-phenylcarbamoyloxy-3c.6t.8.8-tetramethyl-(8arH)-octahydro-3H-3at.7t-methano-azulene

1,4-diphenyl-1,3-butadiyne

methyl cedryl ether

Refernces

• 1、 Shinde, Sandip S.,Navale, Govinda R.,Said, Madhukar S.,Thulasiram, Hirekodathakallu V.. "Stereoselective quenching of cedryl carbocation in epicedrol biosynthesis". supporting information. p. 1161 - 1164. Retrieved 2016/03/09.