Capsanthin

Capsanthin
Names
	IUPAC name (3R,3′S,5′R)-3,3′-Dihydroxy-β,κ-caroten-6′-one
	Systematic IUPAC name (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
Identifiers
CAS Number	465-42-9;
3D model (JSmol)	Interactive image;
Beilstein Reference	2493991
ChEBI	CHEBI:3375;
ChEMBL	ChEMBL1519371;
ChemSpider	4444640;
ECHA InfoCard	100.006.696
EC Number	207-364-1;
E number	E160c(i) (colours)
KEGG	C08584;
PubChem CID	5281228;
UNII	420NY1J57N;
CompTox Dashboard (EPA)	DTXSID10905012 ;
	InChI InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t34-,35+,40+/m1/s1 Key: VYIRVAXUEZSDNC-RDJLEWNRSA-N;
	SMILES CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(=O)[C@@]2(C[C@H](CC2(C)C)O)C)/C)/C;
Properties
Chemical formula	C40H56O3
Molar mass	584.885 g·mol−1
Appearance	Deep red solid
Melting point	181–182 °C (358–360 °F; 454–455 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Capsanthin is a natural red dye of the xanthophyll class of carotenoids. As a food coloring, it has the E number E160c(i). Capsanthin is the main carotenoid in the Capsicum annuum species of plants including red bell pepper, New Mexico chile, and cayenne peppers (Capsicum annuum) and a component of paprika oleoresin.^[1] Capsanthin is also found in some species of lily.^[2]

Capsanthin has antioxidant capacity in vitro due to the presence of eleven conjugated double bonds, a conjugated keto group, and a cyclopentane ring.^[3]^[4]

References

1 2 3 Merck Index (12th ed.). p. 288. Record 1812.
↑ Valadon, L. R. G.; Mummery, Rosemary S. (1977-01-01). "Carotenoids of Lilies and of Red Pepper: Biogenesis of Capsanthin and Capsorubin". Zeitschrift für Pflanzenphysiologie. 82 (5): 407–416. doi:10.1016/S0044-328X(77)80004-4. ISSN 0044-328X.
↑ Hirayama, Osamu; Nakamura, Kyoko; Hamada, Syoko; Kobayasi, Yoko (February 1994). "Singlet oxygen quenching ability of naturally occurring carotenoids". Lipids. 29 (2): 149–150. doi:10.1007/BF02537155. ISSN 0024-4201. PMID 8152349. S2CID 3965039.
↑ Pérez-Gálvez, Antonio; Martin, Hans D.; Sies, Helmut; Stahl, Wilhelm (June 2003). "Incorporation of carotenoids from paprika oleoresin into human chylomicrons". British Journal of Nutrition. 89 (6): 787–793. doi:10.1079/BJN2003842. ISSN 0007-1145. PMID 12828795.

[MerckIndex-1] 1 2 3 Merck Index (12th ed.). p. 288. Record 1812.

[2] Valadon, L. R. G.; Mummery, Rosemary S. (1977-01-01). "Carotenoids of Lilies and of Red Pepper: Biogenesis of Capsanthin and Capsorubin". Zeitschrift für Pflanzenphysiologie. 82 (5): 407–416. doi:10.1016/S0044-328X(77)80004-4. ISSN 0044-328X.

[3] Hirayama, Osamu; Nakamura, Kyoko; Hamada, Syoko; Kobayasi, Yoko (February 1994). "Singlet oxygen quenching ability of naturally occurring carotenoids". Lipids. 29 (2): 149–150. doi:10.1007/BF02537155. ISSN 0024-4201. PMID 8152349. S2CID 3965039.

[4] Pérez-Gálvez, Antonio; Martin, Hans D.; Sies, Helmut; Stahl, Wilhelm (June 2003). "Incorporation of carotenoids from paprika oleoresin into human chylomicrons". British Journal of Nutrition. 89 (6): 787–793. doi:10.1079/BJN2003842. ISSN 0007-1145. PMID 12828795.

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References