Beta-carotene

β-Carotene (beta-carotene) is an organic, strongly colored red-orange pigment abundant in fungi, plants, and fruits. It is a member of the carotenes, which are terpenoids (isoprenoids), synthesized biochemically from eight isoprene units and thus having 40 carbons.

β-Carotene

Skeletal formula
Ball-and-stick model
Space-filling model
Names
IUPAC name β,β-Carotene
Systematic IUPAC name 1,1′-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohex-1-ene)
Other names Betacarotene (INN), β-Carotene, Food Orange 5, Provitamin A
Identifiers
CAS Number	7235-40-7 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1917416
ChEBI	CHEBI:17579 Y
ChEMBL	ChEMBL1293 Y
ChemSpider	4444129 Y
ECHA InfoCard	100.027.851
EC Number	230-636-6
E number	E160a (colours)
KEGG	C02094
PubChem CID	5280489
UNII	01YAE03M7J Y
CompTox Dashboard (EPA)	DTXSID3020253
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 N Key: OENHQHLEOONYIE-UHFFFAOYSA-N N
SMILES CC2(C)CCCC(\C)=C2\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(/C)CCCC1(C)C
Properties
Chemical formula	C40H56
Molar mass	536.888 g·mol−1
Appearance	Dark orange crystals
Density	1.00 g/cm3
Melting point	183 °C (361 °F; 456 K) decomposes
Boiling point	654.7 °C (1,210.5 °F; 927.9 K) at 760 mmHg (101324 Pa)
Solubility in water	Insoluble
Solubility	Soluble in CS2, benzene, CHCl3, ethanol Insoluble in glycerin
Solubility in dichloromethane	4.51 g/kg (20 °C) = 5.98 g/L (given BCM density of 1.3266 g/cm3 at 20°C)
Solubility in hexane	0.1 g/L
log P	14.764
Vapor pressure	2.71·10−16 mmHg
Refractive index (nD)	1.565
Pharmacology
ATC code	A11CA02 (WHO) D02BB01 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H412
Precautionary statements	P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P501
NFPA 704 (fire diamond)	0 1 0
Flash point	103 °C (217 °F; 376 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Dietary β-carotene is a provitamin A compound, converting in the body to retinol (vitamin A). In foods, it has rich content in carrots, pumpkin, spinach, and sweet potato. It is used as a dietary supplement and may be prescribed to treat erythropoietic protoporphyria, an inherited condition of sunlight sensitivity.

β-carotene is the most common carotenoid in plants. When used as a food coloring, it has the E number E160a. The structure was deduced in 1930.

Isolation of β-carotene from fruits abundant in carotenoids is commonly done using column chromatography. It is industrially extracted from richer sources such as the algae Dunaliella salina. The separation of β-carotene from the mixture of other carotenoids is based on the polarity of a compound. β-Carotene is a non-polar compound, so it is separated with a non-polar solvent such as hexane. Being highly conjugated, it is deeply colored, and as a hydrocarbon lacking functional groups, it is lipophilic.