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R3375

Retinyl palmitate

Name: Retinyl palmitate
Brand: SIGMA

Type IV, ~1,800,000 USP units/g, oil

Synonym(s):

Vitamin A palmitate, all−trans−Retinol palmitate

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About This Item

Empirical Formula (Hill Notation):

C₃₆H₆₀O₂

CAS Number:

79-81-2

Molecular Weight:

524.86

UNSPSC Code:

12352205

NACRES:

NA.79

PubChem Substance ID:

24899361

EC Number:

201-228-5

Beilstein/REAXYS Number:

1917366

MDL number:

MFCD00019414

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Properties

biological source

synthetic (organic)

Quality Level

100

type

Type IV

assay

≥90% (HPLC)

form

oil

specific activity

~1,800,000 USP units/g

color

yellow to orange

mp

26 °C

storage temp.

2-8°C

SMILES string

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

InChI

1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+

InChI key

VYGQUTWHTHXGQB-FFHKNEKCSA-N

Description

General description

Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A, respectively. The retinoids comprise a cyclohexenyl ring with a 20-carbon with double bonds in cis and trans configuration. Retinyl palmitate is a major storage form of vitamin A. Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as needed. Retinoids also exist as retinyl esters such as retinyl propionate, retinyl acetate and retinyl palmitate.

Application

Retinyl palmitate has been used as:

a retinoid derivative to modulate expression of connexin Cx26 and Cx30 in the cochlea
a standard in high performance liquid chromatography(HPLC)
as a retinoid substrate in the isomerase assay of eyecup protein homogenates

Biochem/physiol Actions

Retinoids are ligands to nuclear receptors and have antioxidant functionality. Retinyl palmitate is widely used in pharmaceutical and cosmetic applications. In sunscreen, it protects from UVB-induced DNA damage and apoptosis. Retinyl palmitate is used to treat photoaging in skincare cosmetics. Retinyl palmitate is an effective chemopreventive agent to treat lung cancer. It also regulates various biological processes including cell differentiation and proliferation.

Review: Vitamin A metabolism.

Packaging

Sealed ampule.

Physical form

Oil at room temperature

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pictograms

GHS08

signalword

Danger

hcodes

H360D,H412

pcodes

P202 - P273 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Aquatic Chronic 3 - Repr. 1B

Storage Class

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

wgk

WGK 2

flash_point_f

No data available

flash_point_c

No data available

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Global Trade Item Number

SKU	GTIN
R3375-100G	04061836695033
R3375-1G	04061835548231
R3375-5G	04061835548248