Xanthorrhizol

Base Information

• Chemical Name: Xanthorrhizol
• CAS No.: 30199-26-9
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.339
• European Community (EC) Number: 250-090-2
• DSSTox Substance ID: DTXSID20184290
• Nikkaji Number: J19.206F
• Wikidata: Q72470562
• Metabolomics Workbench ID: 135885
• ChEMBL ID: CHEMBL460033
• Mol file: 30199-26-9.mol

Synonyms:xanthorrhizol;xanthorrizol

Chemical Property of Xanthorrhizol

Chemical Property:

• Vapor Pressure: 0.00011mmHg at 25°C
• Refractive Index: 1.522
• Boiling Point: 326.9 °C at 760 mmHg
• PKA: 10.34±0.10(Predicted)
• Flash Point: 147.2 °C
• PSA: 20.23000
• Density: 0.948 g/cm³
• LogP: 4.55050
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 228

Purity/Quality:

98%Min ^*data from raw suppliers

Xanthorrhizol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60
• Safety Statements: 53-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)C(C)CCC=C(C)C)O
• Isomeric SMILES: CC1=C(C=C(C=C1)[C@H](C)CCC=C(C)C)O
• Uses: Xanthorrhizol is a nautral sesquiterpenoid from the rhizome of Curcuma xanthorrhiza that induces apoptosis and growth arrest in HCT116 human colon cancer cells.

Technology Process of Xanthorrhizol

There total 28 articles about Xanthorrhizol 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: 91.0%

(R)-2-methoxy-1-methyl-4-(6-methylhept-5-en-2-yl)benzene (30199-27-0) → (R)-(-)-xanthorrhizol (59684-62-7,97372-52-6,137881-42-6,30199-26-9)

Guidance literature:

(R)-2-methoxy-1-methyl-4-(6-methylhept-5-en-2-yl)benzene; With sodium β-(diethyalmino)ethylmercaptide; In N,N-dimethyl-formamide; for 10h; Inert atmosphere; Reflux;

With hydrogenchloride; In water; N,N-dimethyl-formamide; Inert atmosphere;

DOI:10.1002/anie.201107802

Reference yield: 47.0%

2-methyl-5-((R)-6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol (915301-61-0) → (R)-(-)-xanthorrhizol (59684-62-7,97372-52-6,137881-42-6,30199-26-9)

Guidance literature:

2-methyl-5-((R)-6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol; With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 5.5h;

With methanesulfonyl chloride; triethylamine; In dichloromethane; 0 deg C to rt then reflux 7 h;

With potassium hydroxide; In methanol; for 7h; Heating;

DOI:10.1016/j.tetlet.2006.11.135

Reference yield: 15.963%

C19H29NO2 → (R)-(-)-xanthorrhizol (59684-62-7,97372-52-6,137881-42-6,30199-26-9)

Guidance literature:

With sodium hydroxide; In water; isopropyl alcohol; at 50 - 55 ℃; for 2h;

upstream raw materials:

(R)-2-methoxy-1-methyl-4-(6-methylhept-5-en-2-yl)benzene

2-methyl-5-((R)-6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol

6-hydroxy-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enone

4-[(1R)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one

Downstream raw materials:

(R)-2-methoxy-1-methyl-4-(6-methylhept-5-en-2-yl)benzene

12,13-epoxyxanthorrhizol

2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]benzene-1,4-diol

C₂₂H₃₀O₃

Refernces

• 1、 Liu, Feipeng,Zhong, Jiangchun,Zhou, Yun,Gao, Zidong,Walsh, Patrick J.,Wang, Xueyang,Ma, Sijie,Hou, Shicong,Liu, Shangzhong,Wang, Minan,Wang, Min,Bian, Qinghua. "Cobalt-Catalyzed Enantioselective Negishi Cross-Coupling of Racemic α-Bromo Esters with Arylzincs". supporting information. p. 2059 - 2064. Retrieved 2018/02/14.
• 2、 Song, Song,Zhu, Shou-Fei,Yang, Shuang,Li, Shen,Zhou, Qi-Lin. "Enantioselective iridium-catalyzed hydrogenation of β,γ- unsaturated carboxylic acids: An efficient approach to chiral 4-alkyl-4-aryl butanoic acids". supporting information; experimental part. p. 2708 - 2711. Retrieved 2012/04/17.