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Key Documents

R7882

Sigma-Aldrich

Retinyl acetate

BioReagent, solid or viscous liquid, synthetic, suitable for cell culture

Synonym(s):

Retinol acetate, Vitamin A acetate

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About This Item

Empirical Formula (Hill Notation):
C22H32O2
CAS Number:
Molecular Weight:
328.49
Beilstein:
1915439
EC Number:
MDL number:
UNSPSC Code:
12352205
eCl@ss:
34058009
PubChem Substance ID:
NACRES:
NA.75

biological source

synthetic

product line

BioReagent

Assay

≥90% (HPLC)

form

solid or viscous liquid

potency

~2,800,000 I.U. per g

mol wt

Mw 328.49 g/mol

technique(s)

cell culture | mammalian: suitable

color

light yellow to dark yellow

mp

57-58 °C

solubility

absolute ethanol: 25 mg/mL (lit.)

storage temp.

−20°C

SMILES string

CC1=C(/C=C/C(C)=C/C=C/C(C)=C/COC(C)=O)C(C)(C)CCC1

InChI

1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9+,18-14+

InChI key

QGNJRVVDBSJHIZ-QHLGVNSISA-N

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General description

Retinyl-acetate is a natural and ester derivative of vitamin A. It is found in classical media formulations such as M-199; NCTC-109 and William′s Medium E. Vitamin A is a component of serum useful in most serum containing cell culture systems, which receive some level of vitamin A.

Application

Retinyl acetate has been used as a standard to measure the concentration of vitamin C in high performance liquid chromatography analysis (HPLC) and as a supplement in the preparation of the complete medium.

Biochem/physiol Actions

The oxidized form of retinol is retinoic acid, which has hormone-like growth factor and differentiation activity for epithelial and related cell types, especially neural cells. Retinoic acid induces embryonic stem cells to differentiate towards neural cells. Retinyl-acetate is known to be effective in treating breast cancer.

Other Notes

All trans

Preparation Note

The melting point of this material is approx. 58 °C. In order to package, it was melted and may exist as a crystalline solid or as a supercooled viscous liquid.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Aquatic Chronic 4 - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Changes in the composition of yak colostrum during the first week of lactation
Mi JD, et al.
Journal of Dairy Science, 99(1), 818-824 (2016)
Hormones and Vitamins in Cancer Treatment, 247-247 (1990)
Using an adherent cell culture of the mouse subependymal zone to study the behavior of adult neural stem cells on a single-cell level
Ortega F, et al.
Nature Protocols, 6(12), 1847-1847 (2011)
Ling Zhang et al.
Nature, 464(7291), 1058-1061 (2010-03-30)
Cancer chemoprevention uses natural, synthetic, or biological substances to reverse, suppress, or prevent either the initial phase of carcinogenesis or the progression of neoplastic cells to cancer. It holds promise for overcoming problems associated with the treatment of late-stage cancers.
Avash J Singh et al.
Pediatric research, 67(6), 619-623 (2010-03-11)
Chronic lung disease (CLD) is a major cause of long-term morbidity in extremely LBW infants with respiratory distress syndrome. Parenteral vitamin A administration decreases the risk of CLD. We tested the hypothesis that intratracheal vitamin A administration with surfactant is

Articles

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

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