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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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Synthetic 9-cis-beta-carotene inhibits photoreceptor degeneration in cultures of eye cups from rpe65rd12 mouse model of retinoid cycle defect
Sher I, et al.
Scientific Reports, 8(1), 6130-6130 (2018)
T Toba et al.
Life sciences, 61(8), 839-845 (1997-01-01)
The aim of the present study was to determine to what extent 9-cis beta-carotene, one of the most abundant naturally-occurring cis-isomers of beta-carotene, can inhibit the growth of cervical dysplasia-derived cells in comparison with all-trans beta-carotene. We found that 9-cis
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)
Treatment With 9-cis beta-Carotene-Rich Powder in Patients With Retinitis Pigmentosa: A Randomized Crossover Trial
Rotenstreich Y, et al.
JAMA Ophthalmology, 131(8), 985-992 (2013)
G Levin et al.
Nutrition and cancer, 27(3), 293-297 (1997-01-01)
It has been implied that the antiperoxidative activity of beta-carotene is important for its ability to prevent malignant and cardiovascular diseases. In vitro studies have shown that 9-cis beta-carotene is a better antioxidant than the all-trans isomer. In the present
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