gamma-Carotene

Base Information

• Chemical Name: gamma-Carotene
• CAS No.: 472-93-5
• Deprecated CAS: 10323-83-8,10593-83-6
• Molecular Formula: C40H56
• Molecular Weight: 536.885
• UNII: DH369M0SOE
• DSSTox Substance ID: DTXSID70897429
• Metabolomics Workbench ID: 28985
• Nikkaji Number: J5.953F
• Wikidata: Q5520255
• Wikipedia: %CE%93-Carotene
• Mol file: 472-93-5.mol

Synonyms:GAMMA-CAROTENE;472-93-5;beta,psi-Carotene;DH369M0SOE;2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaenyl]-1,3,3-trimethylcyclohexene;UNII-DH369M0SOE;gamma-Carotin;.GAMMA.-CAROTENE;gamma-Carotene, all-trans-;.BETA.,.PSI.-CAROTENE;.GAMMA.-CAROTENE [MI];CHEBI:27740;DTXSID70897429;gamma-Carotene, >=90% (HPLC);LMPR01070260;.GAMMA.-CAROTENE, ALL-TRANS-;C05435;Q5520255;(ALL-E)-2-(3,7,12,16,20,24-HEXAMETHYL-1,3,5,7,9,11,13,15,17,19,23-PENTACOSAUNDECAENYL)-1,3,3-TRIMETHYLCYCLOHEXENE;2-(3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaenyl)-1,3,3-trimethylcyclohexene;CYCLOHEXENE, 2-(3,7,12,16,20,24-HEXAMETHYL-1,3,5,7,9,11,13,15,17,19,23-PENTACOSAUNDECAENYL)-1,3,3-TRIMETHYL-, (ALL-E)-

Chemical Property of gamma-Carotene

Chemical Property:

• Vapor Pressure: 1.89E-16mmHg at 25°C
• Melting Point: 152-153.5°; mp 177.5°
• Refractive Index: 1.5630 (estimate)
• Boiling Point: 657.8°Cat760mmHg
• Flash Point: 348.4°C
• PSA: 0.00000
• Density: 0.914g/cm³
• LogP: 12.77190
• Storage Temp.: -20°C
• XLogP3: 14.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 13
• Exact Mass: 536.438201786
• Heavy Atom Count: 40
• Complexity: 1180

Purity/Quality:

98%,99%, ^*data from raw suppliers

γ-Carotene ≥90% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C=C(\C)/CCC=C(C)C)/C)/C
• Uses: γ-Carotene may be used as a reference standard in the determination of γ-carotene in fruits using high performance liquid chromatography coupled with diode array detector (HPLC-DAD) and mass spectrometry (HPLC-MS).

Technology Process of gamma-Carotene

There total 25 articles about gamma-Carotene 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: 53.0%

trimethylaluminum (75-24-1) + 6,10,14-trimethyl-3E,5E,7E,9E,13-pentadecapentaen-1-yne + 1-((E,E,E,E,E)-3,7-dimethyl-10-bromo-1,3,5,7,9-decapentaenyl)-2,6,6-trimethyl-1-cyclohexene → trans-gamma-Carotene (472-93-5)

Guidance literature:

trimethylaluminum; 6,10,14-trimethyl-3E,5E,7E,9E,13-pentadecapentaen-1-yne; With zirconocene dichloride; In dichloromethane; at 23 ℃; for 4h;

at 50 ℃;

1-((E,E,E,E,E)-3,7-dimethyl-10-bromo-1,3,5,7,9-decapentaenyl)-2,6,6-trimethyl-1-cyclohexene; With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; zinc(II) chloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 23 ℃; for 6h; Further stages.;

DOI:10.1021/ol000384y

Reference yield: 2.0%

(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal (103956-99-6,1071-52-9) + C33H38BrP → trans-gamma-Carotene (472-93-5)

Guidance literature:

With sodium methylate; In methanol; N,N-dimethyl-formamide; for 3h; Ambient temperature;

DOI:10.1002/hlca.19850680604

Reference yield:

6,10-dimethyl-3E,5E,9-undecatrien-1-yne (331258-03-8) → trans-gamma-Carotene (472-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 69 percent

2.1: Cp₂ZrCl₂ / 1,2-dichloro-ethane / 12 h / 20 °C

2.2: 53 percent / TFP; ZnCl₂ / Pd₂(dba)3 / tetrahydrofuran; dimethylformamide / 5 h / 20 °C

zirconocene dichloride; In 1,2-dichloro-ethane;

DOI:10.1021/ol000384y

upstream raw materials:

γ-carotene

(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

15,15'-Dehydro-γ-carotin

Downstream raw materials:

β,ψ-caroten-4-one

(+/-)-β,ψ-caroten-4-ol

Refernces

• 1、 Zeng,Negishi. "A novel, selective, and efficient route to carotenoids and related natural products via Zr-catalyzed carboalumination and Pd- and Zn-catalyzed cross coupling.". . p. 719 - 722. Retrieved 2007/10/03.