1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene

• ChemBase ID: 72800
• Molecular Formular: C40H56
• Molecular Mass: 536.87264
• Monoisotopic Mass: 536.43820179
• SMILES: C1CCC(C(=C1C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(CCCC1(C)C)C)\C)\C)/C)/C)(C)C
• Canonical SMILES: C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)CCCC1(C)C)/C)/C)/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C
• InChI: InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+
• InChIKey: OENHQHLEOONYIE-JLTXGRSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene; 1,3,3-trimethyl-2-[3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene
• IUPAC Traditional name: β-carotene
• Synonyms: β; β-Carotene; Provitamin A; Solatene; β-Ca; Beta carotene; Provitamin A₁; β-CAROTENE PREDOMINANTLY trans; (all-E)-1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethylcyclohexene]; β,β-Carotene; all-trans-β-Carotene; BetaVit; Betacarotene; Carotaben; Carotene Base 80S; NSC 62794; Provatene; Provatenol; Rovimix β-Carotene; β-Carotene; β-Carotene; β-CAROTENE; β,β-胡萝卜素; 维生素原 A; β-胡萝卜素

Database IDs

• CAS Number: 7235-40-7
• EC Number: 230-636-6
• MDL Number: MFCD00001556
• Beilstein Number: 1917416
• PubChem SID: 162037721; 24892702; 24893189
• PubChem CID: 5280489

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 11.124081
• LogD (pH = 7.4): 11.124081
• Log P: 11.124081
• Molar Refractivity: 191.6118 cm^3
• Polarizability: 70.62342 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble30 μg/mL; H2O: insoluble; hexane: soluble1.1 mg/mL; hexane: soluble100 μg/mL
• Apperance: dark red to brown powder; red to purple crystalline
• Melting Point: 178-179°C; 178-183°C
• Flash Point: 103 °C; 217.4 °F
• Absorption Wavelength: ε1%/450 nm, hexane 2450-2590 (vs. 2590, lit.); ε1%/478 nm, hexane 2160-2280 (vs. 2280, lit.)

Safety Information

• Storage Condition: 0°C, Store Under Nitrogen, Protect from light; -20°C; Amber Vial, -20°C Freezer
• RTECS: FI0329500
• German water hazard class: 1
• Risk Statements: 44
• Safety Statements: 7-15-18
• Personal Protective Equipment: Eyeshields, Gloves
• Supplemental Hazard Statements: Risk of explosion if heated under confinement.
• Storage Temperature: -20°C

Product Information

• Purity: ≥93% (UV); ≥95% (HPLC)
• Salt Data: Free Base
• Potency: ~1,600,000 units vitamin A per g
• Impurities: α-carotene, essentially free
• Biological Source: synthetic
• Type: Type I; Type II

DETAILS

MP Biomedicals - 02193459

Dry Powder

MP Biomedicals - 02101287

Crystalline
Synthetic
Predominantly the trans-β-isomer

Selleck Chemicals - S1767

Research Area: Metabolic Disease
Biological Activity:
Beta Carotene is an organic compound and classified as a terpenoid. It is a precursor (inactive form) of vitamin A. Its actions are involved in cancer, cognition photosensitivity. [1]

Sigma Aldrich - C4582

Biochem/physiol Actions
维生素原 A，即 β-胡萝卜素能分类作为抗氧化剂的最重要的原因就是它可以在体外抑制自由基引发的过氧化。然而，它在体内究竟表现为抗氧化剂或是促氧化剂却取决于细胞环境。它可以降低许多癌症的发病率，却会增加吸烟者患肺癌的几率。

Sigma Aldrich - C9750

包装
Packaged in serum vials.
Biochem/physiol Actions
维生素原 A，即 β-胡萝卜素能分类作为抗氧化剂的最重要的原因就是它可以在体外抑制自由基引发的过氧化。然而，它在体内究竟表现为抗氧化剂或是促氧化剂却取决于细胞环境。它可以降低许多癌症的发病率，却会增加吸烟者患肺癌的几率。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C9750.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C184250

Most important of the provitamins A. Widely distributed in the plant and animal kingdom. In plants it occurs almost always together with chlorophyll. Vitamin A precursor. Ultraviolet screen.

REFERENCES

• http://en.wikipedia.org/wiki/Beta-Carotene
• Karrer, et al.: Helv. Chim. Acta, 12, 1142 (1929)
• Fischli, M., et al.: Helv. Chim. Acta, 58, 1584 (1929)
• Desmet, J., et al.: Biochem. Biophys. Acta, 912, 211 (1929)
• Tan, C., et al.: Food Chem., 92, 661 (1929)
• Chu, B., et al.: J. Agric. Food Chem., 55