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R3375

Sigma-Aldrich

Retinyl palmitate

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
Beilstein/REAXYS Number:
1917366
EC Number:
201-228-5
MDL number:
MFCD00019414
UNSPSC Code:
12352200
PubChem Substance ID:
24899361
NACRES:
NA.79

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

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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

pictograms

Health hazard
GHS08

signalword

Danger

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_germany

WGK 2

flash_point_f

No data available

flash_point_c

No data available

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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Retinoids in cosmeceuticals
Sorg O, et al.
Dermatologic Therapy, 19(5), 289-296 (2006)
Vitamin A or E and a catechin synergize as vaccine adjuvant to enhance immune responses in mice by induction of early interleukin-15 but not interleukin-1beta responses
Patel S, et al.
Immunology, 148(4), 352-362 (2016)
Effects of retinoid treatment on cochlear development, connexin expression and hearing thresholds in mice
Kim Y and Lin X
Journal of Otorhinolaryngology, Hearing and Balance Medicine settings, 1(1), 2-2 (2018)
Laboratory evaluation during high-dose vitamin A administration: a randomized study on lung cancer patients after surgical resection
Infante M, et al.
Journal of Cancer Research and Clinical Oncology, 117(2), 156-162 (1991)
Safety of retinyl palmitate in sunscreens: a critical analysis
Wang SQ, et al.
Journal of the American Academy of Dermatology, 63(5), 903-906 (2010)
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Articles

Retinoic Acid and Gene Expression

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.

Retinoic Acid and Gene Expression

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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