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19081

Sigma-Aldrich

Capsanthin

≥90.0% (HPLC)

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Synonym(s):
(3R,3′S,5′R)-3,3′-Dihydroxy-β,κ-caroten-6′-one
Empirical Formula (Hill Notation):
C40H56O3
CAS Number:
465-42-9
Molecular Weight:
584.87
EC Number:
207-364-1
UNSPSC Code:
12352202
PubChem Substance ID:
329751805
NACRES:
NA.32

Quality Level

100

Assay

≥90.0% (HPLC)

form

powder

λ

in hexane (with 2% dichloromethane)

UV absorption

λ: 467-471 nm Amax

storage temp.

−20°C

SMILES string

CC(/C=C/C1=C(C)C[C@@H](O)CC1(C)C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(\C=C\C([C@@]2(C)C(C)(C)C[C@H](O)C2)=O)C

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

InChI key

VYIRVAXUEZSDNC-RDJLEWNRSA-N

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General description

Capsanthin is a natural red-orange pigment present in red paprika and is a member of the xanthophylls, oxygen-containing carotenoids family. It is made up of a keto group conjugated with a long chain of 11 dienes.

Application

Capsanthin has been used as a reference standard to determine the oral toxicity of saponified Capsicum annum extract with 50% capsanthin by the high-performance liquid chromatography (HPLC) method.

Biochem/physiol Actions

Capsanthin is the last product of the pepper carotenoid biosynthesis pathway. It promotes lipid solubility by esterification with short-chain fatty acids. Capsanthin exhibits anti-oxidant, singlet oxygen quenching ability, antitumor, anti-inflammatory, antidiabetic, chemopreventive, and skin photo-protective activities. In addition, it also possesses anti-hyperlipidemic, anti-obesity, and anti-adipogenic properties. Capsanthin due to its wide array of health benefits is used in the cosmetic, pharma, and nutraceutical industries.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Analysis , bioavailability, and potential healthy effects of capsanthin, natural red pigment from Capsicum spp.
Food Reviews International, 25(3), 198-213 (2009)
Shi-Lin Tian et al.
BMC plant biology, 14, 314-314 (2014-11-19)
There are many varieties of carotenoids in pepper fruits. Capsanthin is a red carotenoid that gives mature pepper fruits their red color. The red color in pepper fruits is regulated mainly by the genes capsanthin/capsorubin synthase(Ccs), phytoene synthase(Psy), lycopene-β-cyclase(Lcyb) and
Alicia Marín et al.
Journal of agricultural and food chemistry, 52(12), 3861-3869 (2004-06-10)
Sweet peppers (Capsicum annuum L.) cv. Vergasa have been studied at four maturity stages (immature green, green, immature red, and red). The individual phenolics (hydroxycinnamic acids and flavonoids), vitamin C (ascorbic acid and dehydroascorbic acid), and individual carotenoids were characterized
E Kotake-Nara et al.
The Journal of nutrition, 131(12), 3303-3306 (2001-12-12)
We investigated whether various carotenoids present in foodstuffs were potentially involved in cancer-preventing action on human prostate cancer. The effects of 15 kinds of carotenoids on the viability of three lines of human prostate cancer cells, PC-3, DU 145 and
Elisabet Fernández-García et al.
Food chemistry, 221, 1317-1321 (2016-12-17)
Carotenoids refer to a wide class of lipophilic pigments synthesized by plants, exert photoprotective and antioxidant properties that are lost upon carotenoid degradation. Their inclusion into hydrophilic host-molecules could improve their stability. Cyclodextrins, provide a hydrophobic cavity in the core
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