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73342

Sigma-Aldrich

β-Carotene 5,6-epoxide

≥85.0% (HPLC)

Synonym(s):

(5RS,6RS)-5,6-Epoxy-5,6-dihydro-β,β-carotene

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About This Item

Empirical Formula (Hill Notation):
C40H56O
CAS Number:
1923-89-3
Molecular Weight:
552.87
UNSPSC Code:
12352202
PubChem Substance ID:
329764813
NACRES:
NA.32

Assay

≥85.0% (HPLC)

form

powder

λ

in hexane (with 2% dichloromethane)

UV absorption

λ: 443-447 nm Amax

storage temp.

−20°C

SMILES string

CC(/C=C/C1=C(C)CCCC1(C)C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(\C=C\C23C(C)(C)CCCC2(O3)C)C

InChI

1S/C40H56O/c1-31(19-13-21-33(3)24-25-36-35(5)23-15-27-37(36,6)7)17-11-12-18-32(2)20-14-22-34(4)26-30-40-38(8,9)28-16-29-39(40,10)41-40/h11-14,17-22,24-26,30H,15-16,23,27-29H2,1-10H3/b12-11+,19-13+,20-14+,25-24+,30-26+,31-17+,32-18+,33-21+,34-22+

InChI key

RVCRIPILOFSMFG-WWSVUWEKSA-N

General description

The 5,6-epoxy structure can give rise to a wide variety of carotenoid end-groups with the plausible biosynthetic transformations of the 5,6-epoxy-ß-ring to give diverse structures such as the cyclopentane carotenoids capsanthin and capsorubin, the retro-carotenoids eschscholtz- xanthin and rhodoxanthin, allenic carotenoids like the neoxanthin and fucoxanthin, 5,6-diols like the karpoxanthin and latoxanthin, 3,6-poxides as found in eutreptiellanone and cucurbitaxanthin, the 6-hydroxy-γ-ring structure found in prasinoxanthin and nigroxanthin, as well as the 5,6-seco-5,6-dione-end-group of semi-ß-carotenone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ5853
BCCJ5851
BCCF1474
BCBT9167
BCBS0794V

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G Martano et al.
Analytical and bioanalytical chemistry, 406(12), 2909-2924 (2014-03-22)
A validated ultrahigh-performance liquid chromatography method using 1.7 μm core-shell particles is presented for the identification and quantification of β-carotene (BC) and related cleavage products (CPs) in primary cell culture media. Besides BC, apo-4'-, apo-8'-, apo-10'-, and apo-12'-carotenals, as well
Alessandra Gentili et al.
Journal of agricultural and food chemistry, 63(33), 7428-7439 (2015-08-11)
This paper presents an analytical strategy for a large-scale screening of carotenoids in tomato fruits by exploiting the potentialities of the triple quadrupole-linear ion trap hybrid mass spectrometer (QqQLIT). The method involves separation on C30 reversed-phase column and identification by
Poliana D Gurak et al.
Food chemistry, 147, 160-169 (2013-11-12)
In this study HPLC-DAD-MS/MS was applied for the identification of compounds derived from (all-E)-β-carotene following epoxidation and oxidative cleavage. The consequences on the CIELAB colour parameters and antioxidant capacity (AC) were also evaluated. Five apocarotenoids, three secocarotenoids, seven Z isomers
T A Kennedy et al.
The Journal of biological chemistry, 267(7), 4658-4663 (1992-03-05)
The effect of the partial pressure of oxygen (pO2) on the antioxidant reactions of all-trans-beta, beta-carotene (BC) was investigated in a soybean phosphatidylcholine liposome system. Peroxyl radicals generated by thermolysis of azo-bis(2,4-dimethylvaleronitrile) at 37 degrees C initiated lipid peroxidation. BC
Oxidative degradation of ?-carotene and ?-apo-8'-carotenal
Mordi, R.C., et al.
Tetrahedron, 49, 911-928 (1993)
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