α-Carotene

Names

[ Name ]:
α-Carotene

[Synonym ]:
1,3,3-Triméthyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tétraméthyl-18-(2,6,6-triméthyl-2-cyclohexén-1-yl)-1,3,5,7,9,11,13,15,17-octadécanonaèn-1-yl]cyclohexène
CISALPHA-CAROTENE
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-2-cyclohexen-1-yl)-1,3,5,7,9,11,13,15,17-octadecanonaen-1-yl]cyclohexen
Renieratene
(6'R)-beta,epsilon-carotene
Isorenieratene
A-CAROTENE
MFCD00136012
CAROTENE,A
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-2-cyclohexen-1-yl)-1,3,5,7,9,11,13,15,17-octadecanonaen-1-yl]cyclohexene
all-trans-α-carotene
β,β-Carotene, 4,5-didehydro-5,6-dihydro-
4,5-Didehydro-5,6-dihydro-β,β-carotene
(+)-α-Carotene

Biological Activity

[Description]:

α-Carotene, a precursor of vitamin A, is used as an anti-metastatic agent or as an adjuvant for anti-cancer drugs. α-Carotene is isolated from yellow-orange and dark-green vegetables[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

α-Carotene (0.5-2.5 μM; 24 hours) significantly increases protein expression of TIMP-1 and TIMP-2 in a concentration-dependent manner in LLC cells. AC (0.5-2.5 μM) significantly increases PAI-1 protein expression. α-Carotene (2.5 μM) also significantly inhibits integrin β1-mediated phosphorylation of focal adhesion kinase (FAK) which then decreased the phosphorylation of MAPK family[2]. α-Carotene (0.5, 1, 2.5 μM; 48 hours) significantly and concentration-dependently inhibits invasion of LLC during 48 h of incubation[2]. α-Carotene (0.5, 1, 2.5 μM; 24 hours) significantly decreases activities of MMP-9, -2 and uPA in concentration-dependent manner in LLC cells[2]. α-Carotene (2, 5, 10 μM; 7 days) inhibits the proliferation of the human neuroblastoma cell line GOTO in a dose- and time-dependent manner. α-Carotene (5 μM; 48 hours) halts the cell cycle at the G0/G1 phase concomitantly with a reduction in the mRNA expression of the protooncogene N-Myc[3]. Western Blot Analysis[2] Cell Line: Lewis lung carcinoma (LLC) cells Concentration: 0.5, 1, 2.5 μM Incubation Time: 24 hours Result: Significantly increased protein expression of TIMP-1 and TIMP-2 in a concentration-dependent manner in LLC cells.

[In Vivo]

α-Carotene (5 mg/kg; oral; twice a week; for additional 3 weeks) alone significantly decreases lung metastasis without affecting primary tumor growth[2]. Animal Model: C57BL/6 male mice (4 weeks old; 20-25 g) with LLC cells[2] Dosage: 5 mg/kg Administration: Oral; twice a week; for additional 3 weeks Result: Significantly decreased lung metastasis.

[References]

[1]. Bushway, R.J., et al. Determination of α- and β-carotene in fruit and vegetables by high performance liquid chromatography. Can. Inst. Food Sci. Technol. J. 15(3), 165-169 (1982).

[2]. Liu YZ, et al. Alpha-carotene inhibits metastasis in Lewis lung carcinoma in vitro, and suppresses lungmetastasis and tumor growth in combination with taxol in tumor xenografted C57BL/6 mice. J Nutr Biochem. 2015 Jun;26(6):607-15.

[3]. Murakoshi M, et al. Inhibitory effects of alpha-carotene on proliferation of the human neuroblastoma cell line GOTO. J Natl Cancer Inst. 1989 Nov 1;81(21):1649-52.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
644.9±35.0 °C at 760 mmHg

[ Melting Point ]:
185ºC

[ Molecular Formula ]:
C₄₀H₅₆

[ Molecular Weight ]:
536.873

[ Flash Point ]:
341.2±20.8 °C

[ Exact Mass ]:
536.438232

[ LogP ]:
15.45

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.563

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
40

[ Safety Phrases ]:
S36/37

[ RIDADR ]:
UN 1593 6.1/PG 3

[ Packaging Group ]:
II; III

[ Hazard Class ]:
4.1

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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Studies of adult subjects have found a strong correlation between serum carotenoids and skin carotenoids measured by resonance Raman spectroscopy (RRS). No published studies have examined correlations...