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95140

Sigma-Aldrich

Retinyl acetate

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

Synonym(s):

Retinol acetate, Vitamin A acetate

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About This Item

Empirical Formula (Hill Notation):
C22H32O2
CAS Number:
127-47-9
Molecular Weight:
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

may partially crystallize

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

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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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)
Emmanuel K Aklamati et al.
The Journal of nutrition, 140(9), 1588-1594 (2010-07-28)
A survey indicated that high-dose vitamin A (HD-VA) supplements had no apparent effect on vitamin A (VA) status, assessed by serum retinol concentrations, of Zambian children lt 5 y of age. To explore possible reasons for the lack of response
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.
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
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