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95140

Sigma-Aldrich

Acetato de retinil

concentrate (~50% (w/w) in peanut oil), ~1500 U/mg

Sinónimos:

Acetato de retinol, Acetato de vitamina A

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About This Item

Fórmula empírica (notación de Hill):
C22H32O2
Número de CAS:
127-47-9
Peso molecular:
328.49
Beilstein/REAXYS Number:
1915439
MDL number:
MFCD00019413
UNSPSC Code:
12352200
eCl@ss:
34058009
PubChem Substance ID:
57653653
NACRES:
NA.79

biological source

synthetic

assay

~95% (HPLC)

form

liquid

quality

concentrate (~50% (w/w) in peanut oil)

specific activity

~1500 U/mg

contains

DL-α-tocopherol as stabilizer

color

yellow to very dark yellow

mp

57-58 °C

storage temp.

2-8°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

Vitamin A is also known as retinol. Retinaldehyde, retinoic acid and retinyl esters are the derivatives of retinol. Retinol consists of a 20-carbon molecule. It also contains a cyclohexanyl ring with a side chain of four double bonds and an alcohol end group. Vitamin A is naturally present in the body as retinyl ester and β-carotene. Retinyl acetate, retinyl propionate and retinyl palmitate are analogs of retinol.

Biochem/physiol Actions

Retinyl esters are stored in the liver and get converted to retinol before absorption by the intestine. Retinal plays a role in eye vision as it is a part of rhodopsin. Retinol binds to the retinol binding proteins in the plasma. Retinyl acetate has applications in cosmetology.

Other Notes

isomeric purity: ~95% all-trans- and ~5% 13-cis-isomer
Review: Systematic mode of action of vitamin A

Caution

crystallized product can be liquidified by heating to 65°C

Unit Definition

1 U corresponds to 1 international unit acc. to Ph Eur II, 217 (1983)

Physical form

kann teilweise kristallisieren

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Aquatic Chronic 4 - Repr. 1B

Storage Class

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

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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Systemic mode of action of vitamin A.
J Ganguly et al.
Vitamins and hormones, 38, 1-54 (1980-01-01)
Retinoids in the treatment of skin aging: an overview of clinical efficacy and safety
Mukherjee S, et al.
Clinical Interventions in Aging, 1(4), 327-327 (2006)
Sunatda Arayachukeat et al.
International journal of pharmaceutics, 404(1-2), 281-288 (2010-11-26)
Retinyl acetate (RA) loaded polymeric nanoparticle (NP) carriers were prepared using two different single polymers, ethyl cellulose (EC) and poly (ethylene glycol)-4-methoxycinnamoylphthaloylchitosan (PCPLC). The stability of RA to aqueous solution and UVA light was significantly improved when encapsulated with PCPLC
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
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.
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