alpha-Carotene

Base Information

• Chemical Name: alpha-Carotene
• CAS No.: 7488-99-5
• Deprecated CAS: 24319-81-1
• Molecular Formula: C40H56
• Molecular Weight: 536.885
• Hs Code.: 32041990
• UNII: 45XWE1Z69V
• DSSTox Substance ID: DTXSID00893691
• Nikkaji Number: J5.728B,J709.300D,J709.301B,J709.302K,J709.303I,J666.574H
• Wikipedia: %CE%91-Carotene
• Wikidata: Q142871
• NCI Thesaurus Code: C68304
• Metabolomics Workbench ID: 28788
• Mol file: 7488-99-5.mol

Synonyms:alpha-carotene;alpha-carotene, (6'R)-isomer

Chemical Property of alpha-Carotene

Chemical Property:

• Vapor Pressure: 8.15E-16mmHg at 25°C
• Melting Point: 185oC
• Refractive Index: 1.5630 (estimate)
• Boiling Point: 644.9oC at 760 mmHg
• Flash Point: 341.2oC
• PSA: 0.00000
• Density: 1.00 g/cm3 (20oC)
• LogP: 12.46170
• Storage Temp.: ?20°C
• Solubility.: Chloroform (Slightly)
• XLogP3: 13.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 10
• Exact Mass: 536.438201786
• Heavy Atom Count: 40
• Complexity: 1200

Purity/Quality:

98%, ^*data from raw suppliers

alpha-Carotene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40-67-36/37/38
• Safety Statements: 36/37-24/25-23

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=CC2C(=CCCC2(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@H]2C(=CCCC2(C)C)C)/C)/C
• Recent ClinicalTrials: Physicians' Health Study
• Description: α-Carotene is a precursor of vitamin A that has been found in various fruits and vegetables. It inhibits proliferation of GOTO human neuroblastoma cells more potently than β-carotene and halts the cell cycle at the G0/G1 phase concomitantly with a reduction in the mRNA expression of the protooncogene N-Myc. It is also more potent than β-carotene in mouse models of skin and lung carcinogenesis and decreases the number of hepatomas in mice with spontaneous liver carcinogenesis when administered in drinking water at a concentration of 0.05%. α-Carotene levels are increased in patients with coronary heart disease and are inversely correlated with the risk of estrogen receptor-negative breast cancer.
• Uses: carotene is used to provide a red-orange color in cosmetic formulations. It is the primary yellow coloring component of butter, carrots, and egg yolk. Carotene is found in plants as well as in many animal tissues. Carotene is a colorant and provitamin, being a hydrocarbon which is one of two subgroups of the carotenoids (yellow, orange, or red pig- ments). the other subgroup is xanthophylls. functions as a colorant with beta-apo-8-carotenal being a red-orange carotenoid and betabeing a yellow carotenoid. it is also a vitamin a precursor that is converted by the body to vitamin a. it is used in ice cream, cheese, and other dairy products. (6''R)-β,ε-Carotene is a trans isomer of carotenoid pigment found in plants. It is a terpenoid hydrocarbon.

Technology Process of alpha-Carotene

There total 16 articles about alpha-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:

1,3,3-Trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-cyclohex-1-enyl)-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-cyclohexanol (6060-33-9) → alpha-carotene (7488-99-5)

Guidance literature:

With pyridine; trichlorophosphate;

DOI:10.1016/S0031-9422(00)86070-7

Reference yield:

mutatochrome (15678-54-3) → alpha-carotene (7488-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄

2: POCl₃, Py

With pyridine; lithium aluminium tetrahydride; trichlorophosphate;

DOI:10.1016/S0031-9422(00)86070-7

Reference yield:

(E)-4-octene-2,7-dione (125069-77-4,268750-56-7) + 6-(2-methyl-6,6-dimethylcyclohex-1-en-1-yl)-3-methylhex-1-ene-5-yne-3-ol (74352-11-7) → alpha-carotene (7488-99-5)

Guidance literature:

With diethyl ether; ethylmagnesium bromide; copper(l) chloride; Reagens 4: Toluol; Reagens 5: Lindlar-Katalysator; Reagens 6: Dioxan; Reagens 7: Toluol-4-sulfonsaeure; Reagens 8: Jod; Darstellung ueber mehrere Stufen;

DOI:10.1002/hlca.19550380307

upstream raw materials:

lutein

(E)-β-ionone

9-cis-α-carotene

1,3,3-Trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-cyclohex-1-enyl)-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-cyclohexanol

Downstream raw materials:

beta-carotene

9-cis-α-carotene

4,4-dimethyl-6-oxo-heptanoic acid

2,3,2',3',4',5'-hexadehydro-4,5'-retro-β,β-carotene

Refernces

• 1、 Eugster,Karrer. "". . p. 610. Retrieved 1955.
• 2、 Chen, B. H.,Chen, T. M.,Chien, J. T.. "Kinetic Model for Studying the Isomerization of α- and β-Carotene during Heating and Illumination". . p. 2391 - 2397. Retrieved 2007/10/02.