β-Carotene

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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1917416
ChEBI	CHEBI:17579 ;
ChEMBL	ChEMBL1293 ;
ChemSpider	4444129 ;
ECHA InfoCard	100.027.851
EC Number	230-636-6;
E number	E160a (colours)
KEGG	C02094;
PubChem CID	5280489;
UNII	01YAE03M7J ;
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 Key: OENHQHLEOONYIE-UHFFFAOYSA-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). verify (what is ?) Infobox references

β-Carotene (beta-carotene) is an organic, strongly colored red-orange pigment abundant in fungi,^[7] 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.

Dietary β-carotene is a provitamin A compound, converting in the body to retinol (vitamin A).^[8] In foods, it has rich content in carrots, pumpkin, spinach, and sweet potato.^[8] It is used as a dietary supplement and may be prescribed to treat erythropoietic protoporphyria, an inherited condition of sunlight sensitivity.^[9]

β-carotene is the most common carotenoid in plants.^[8] When used as a food coloring, it has the E number E160a.^[10]^: 119 The structure was deduced in 1930.^[11]

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.^[12] 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.^[13] Being highly conjugated, it is deeply colored, and as a hydrocarbon lacking functional groups, it is lipophilic.

^ ^a ^b Hursthouse MB, Nathani SC, Moss GP (2004). "CSD Entry: CARTEN02". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/cc8j3mh. Retrieved 9 July 2022.
^ ^a ^b Senge MO, Hope H, Smith KM (1992). "Structure and Conformation of Photosynthetic Pigments and Related Compounds 3. Crystal Structure of β-Carotene". Z. Naturforsch. C. 47 (5–6): 474–476. doi:10.1515/znc-1992-0623. S2CID 100905826.
^ "SciFinder – CAS Registry Number 7235-40-7". Retrieved 21 October 2009.
^ ^a ^b Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). CRC Press. p. 3.94. ISBN 978-1439855119.
^ "Beta-carotene". PubChem, US National Library of Medicine. 27 January 2024. Retrieved 31 January 2024.
^ ^a ^b Sigma-Aldrich Co., β-Carotene. Retrieved on 27 May 2014.
^ Lee SC, Ristaino JB, Heitman J (December 2012). "Parallels in Intercellular Communication in Oomycete and Fungal Pathogens of Plants and Humans". PLOS Pathogens. 8 (12): e1003028. doi:10.1371/journal.ppat.1003028. PMC 3521652. PMID 23271965.
^ ^a ^b ^c "α-Carotene, β-Carotene, β-Cryptoxanthin, Lycopene, Lutein, and Zeaxanthin". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. October 2023. Retrieved 31 January 2024.
^ "Beta-carotene". MedlinePlus, National Library of Medicine, US National Institutes of Health. 27 January 2023. Retrieved 31 January 2024.
^ Milne, George W. A. (2005). Gardner's commercially important chemicals: synonyms, trade names, and properties. New York: Wiley-Interscience. ISBN 978-0-471-73518-2.
^ Karrer P, Helfenstein A, Wehrli H (1930). "Pflanzenfarbstoffe XXV. Über die Konstitution des Lycopins und Carotins". Helvetica Chimica Acta. 13 (5): 1084–1099. doi:10.1002/hlca.19300130532.
^ States4439629 United States expired 4439629, Rüegg, Rudolf, "Extraction Process for Beta-Carotene", published 27 March 1984, assigned to Hoffmann-La Roche Inc.
^ Mercadante AZ, Steck A, Pfander H (January 1999). "Carotenoids from guava (Psidium guajava l.): isolation and structure elucidation". Journal of Agricultural and Food Chemistry. 47 (1): 145–51. Bibcode:1999JAFC...47..145M. doi:10.1021/jf980405r. PMID 10563863.

[Hursthouse-1] Hursthouse MB, Nathani SC, Moss GP (2004). "CSD Entry: CARTEN02". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/cc8j3mh. Retrieved 9 July 2022.

[Senge-2] Senge MO, Hope H, Smith KM (1992). "Structure and Conformation of Photosynthetic Pigments and Related Compounds 3. Crystal Structure of β-Carotene". Z. Naturforsch. C. 47 (5–6): 474–476. doi:10.1515/znc-1992-0623. S2CID 100905826.

[Scifinder-3] "SciFinder – CAS Registry Number 7235-40-7". Retrieved 21 October 2009.

[r1-4] Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). CRC Press. p. 3.94. ISBN 978-1439855119.

[pubchem-5] "Beta-carotene". PubChem, US National Library of Medicine. 27 January 2024. Retrieved 31 January 2024.

[sigma-6] Sigma-Aldrich Co., β-Carotene. Retrieved on 27 May 2014.

[:0-7] Lee SC, Ristaino JB, Heitman J (December 2012). "Parallels in Intercellular Communication in Oomycete and Fungal Pathogens of Plants and Humans". PLOS Pathogens. 8 (12): e1003028. doi:10.1371/journal.ppat.1003028. PMC 3521652. PMID 23271965.

[lpi-8] "α-Carotene, β-Carotene, β-Cryptoxanthin, Lycopene, Lutein, and Zeaxanthin". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. October 2023. Retrieved 31 January 2024.

[mlp-9] "Beta-carotene". MedlinePlus, National Library of Medicine, US National Institutes of Health. 27 January 2023. Retrieved 31 January 2024.

[isbn0-471-73518-3-10] Milne, George W. A. (2005). Gardner's commercially important chemicals: synonyms, trade names, and properties. New York: Wiley-Interscience. ISBN 978-0-471-73518-2.

[11] Karrer P, Helfenstein A, Wehrli H (1930). "Pflanzenfarbstoffe XXV. Über die Konstitution des Lycopins und Carotins". Helvetica Chimica Acta. 13 (5): 1084–1099. doi:10.1002/hlca.19300130532.

[us4439629-12] States4439629 United States expired 4439629, Rüegg, Rudolf, "Extraction Process for Beta-Carotene", published 27 March 1984, assigned to Hoffmann-La Roche Inc.

[13] Mercadante AZ, Steck A, Pfander H (January 1999). "Carotenoids from guava (Psidium guajava l.): isolation and structure elucidation". Journal of Agricultural and Food Chemistry. 47 (1): 145–51. Bibcode:1999JAFC...47..145M. doi:10.1021/jf980405r. PMID 10563863.

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