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52824

Sigma-Aldrich

(9Z)-β-Carotene

≥90.0% (HPLC)

Synonym(s):

(9Z)-β-β-Carotene, 9-cis-β-Carotene, Neo-β-carotene U

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About This Item

Empirical Formula (Hill Notation):
C40H56
CAS Number:
13312-52-2
Molecular Weight:
536.87
Beilstein:
3227021
MDL number:
MFCD00870648
UNSPSC Code:
12352211
PubChem Substance ID:
329757890
NACRES:
NA.32

Assay

≥90.0% (HPLC)

form

solid

lipid type

unsaturated FAs

storage temp.

−20°C

SMILES string

CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(C)/C=C/C2=C(C)CCCC2(C)C)C(C)(C)CCC1

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/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21-,34-22+

InChI key

OENHQHLEOONYIE-BVZAMQQESA-N

Biochem/physiol Actions

(9Z)-β-Carotene or 9-cis-β-carotene is a 9-cis retinoic acid precursor in intestinal mucosal glands of humans. 9-cis retinoic acid is a ligand for nuclear receptor and retinoid X receptor (RXR). 9-cis-β-carotene participates in gene regulation. It is majorly present in liver. 9-cis-β-Carotene supplementation inhibits the progression of atherosclerosis. 9-cis-β-carotene may restore photoreceptors in retinitis pigmentosa (RP) and retinal dystrophies.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Prevention of atherosclerosis progression by 9-cis-beta-carotene rich alga Dunaliella in apoE-deficient mice
Harari A, et al.
BioMed Research International, 2013 (2013)
All-trans beta-carotene appears to be more bioavailable than 9-cis or 13-cis beta-carotene in gerbils given single oral doses of each isomer
Deming DM, et al.
The Journal of Nutrition, 132(9), 2700-2708 (2002)
Rathinam Raja et al.
Microbiological research, 162(2), 177-184 (2006-05-23)
The beta-carotene-yielding microalga, Dunaliella salina (Dunal) Teod. maintained in De Walne's medium was harvested and lyophilized. Fibrosarcoma was induced in rats by 20-methylcholanthrene. 0.5 g and 1.0 g of lyophilized D. salina powder was administered to the rats orally through
Changes of carotenoids, color, and vitamin A contents during processing of carrot juice.
Chen, B., et al.
Journal of Agricultural and Food Chemistry, 43, 1912-1918 (1995)
W Stahl et al.
Clinical chemistry, 39(5), 810-814 (1993-05-01)
The analysis of beta-carotene and lycopene, the two predominant carotenoids in human serum and tissues, was extended to the level of geometrical (cis-trans) isomers by using an improved reversed-phase HPLC methodology. We separated five geometrical isomers of beta-carotene and seven
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