R7632

Sigma-Aldrich

Retinol

synthetic, ≥95% (HPLC), crystalline

Synonym(s):
Axerophthol, Vitamin A alcohol, Vitamin A1, Vitamin A, all-trans-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol
Empirical Formula (Hill Notation):
C20H30O
CAS Number:
Molecular Weight:
286.45
Beilstein/REAXYS Number:
403040
EC Number:
MDL number:
eCl@ss:
34058018
PubChem Substance ID:
NACRES:
NA.79

Quality Level

biological source

synthetic

assay

≥95% (HPLC)

form

crystalline

application(s)

HPLC: suitable

color

faint yellow to very dark yellow

mp

61-63 °C (lit.)

ε (extinction coefficient)

2700 u/mg at 326 nm in isopropanol

shipped in

dry ice

storage temp.

−20°C

SMILES string

CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/CO)=C(C)CCC1

InChI

1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChI key

FPIPGXGPPPQFEQ-OVSJKPMPSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

Retinol or vitamin A alcohol is the main circulating form of vitamin A. It is not biologically active. Retinol or all-trans-retinol is a 20-carbon molecule with cyclohexenyl ring, a side chain with four double bonds (in trans configuration), and an alcohol end group.

Application

Retinol has been used:
  • for the synthesis of all-trans-retinoic acid in HepG2 cells
  • to study the effect of retinol on the growth of murine normal colonic cells cultured as organoids
  • as a standard for determination of vitamin A in cells
  • as a component of chemically defined medium for testis organ culture and spermatogenesis in vitro.

Packaging

100, 250, 500 mg in ampule
1 g in ampule
Light protecting glass vial.
Bottomless glass bottle. Contents are inside inserted fused cone.

Biochem/physiol Actions

Retinol and its derivatives exhibit anti-aging properties. In addition, it also acts as an anti-wrinkle agent. However, due to its photoinstability and skin irritation potency, it is not widely used in cosmetic formulations. Retinol is used in the treatment of dermatoses including photoaging. Its deficiency is associated with the development of xerosis and follicular hyperkeratosis.
Retinol works as a precursor of active retinoids. It is converted to retinaldehyde and subsequently to retinoic acid. All-trans and 9-cis-retinoic acid are the ligands for nuclear receptors, retinoic acid receptors (RARs) and retinoid X receptors (RXRs). These receptors are transcriptional regulators of various genes.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R7632.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Certificate of Analysis

Certificate of Origin

Insulin regulates retinol dehydrogenase expression and all-trans-retinoic acid biosynthesis through FoxO1.
Obrochta KM et al.
The Journal of Biological Chemistry, 290, 7259-7259 (2015)
Retinol Promotes In Vitro Growth of Proximal Colon Organoids through a Retinoic Acid-Independent Mechanism.
Matsumoto T et al.
PLoS ONE, 11, e0162049-e0162049 (2016)
Valproate ameliorates nitroglycerin-induced migraine in trigeminal nucleus caudalis in rats through inhibition of NF-?B.
Li Y et al.
The Journal of Headache and Pain, 17, 49-49 (2016)
Understanding the physiological role of retinol-binding protein in vitamin A metabolism using transgenic and knockout mouse models.
Quadro L et al.
Molecular Aspects of Medicine, 24, 421-421 (2003)
A newly synthesized photostable retinol derivative (retinyl N-formyl aspartamate) for photodamaged skin: profilometric evaluation of 24-week study
Lee MS, et al.
Journal of the American Academy of Dermatology, 55(2), 220-224 (2006)
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.
Read More
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.
Read More
Protocols
Separation of δ-Tocopherol, analytical standard; Retinyl acetate; (+)-γ-Tocopherol; α-Tocopherol, ≥95.5%; Retinol; Vitamin A (acetate), meets USP testing specifications.
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.