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52824

Sigma-Aldrich

(9Z)-β-Carotene

≥90.0% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C40H56
Número de CAS:
13312-52-2
Peso molecular:
536.87
Beilstein/REAXYS Number:
3227021
MDL number:
MFCD00870648
UNSPSC Code:
12352211
PubChem Substance ID:
329757890
NACRES:
NA.32

Quality Level

100

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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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