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R7632

Sigma-Aldrich

Retinol

synthetic, ≥95% (HPLC), crystalline

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Synonym(s):
Axerophthol, Vitamin A, Vitamin A alcohol, Vitamin A1, 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:
68-26-8
Molecular Weight:
286.45
Beilstein:
403040
EC Number:
200-683-7
MDL number:
MFCD00001552
eCl@ss:
34058018
PubChem Substance ID:
24899395
NACRES:
NA.79

biological source

synthetic

Assay

≥95% (HPLC)

form

crystalline

specific activity

~2700 U/mg

technique(s)

HPLC: suitable

color

yellow to very dark yellow, to Very Dark Orange

mp

61-63 °C (lit.)

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

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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.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.
Light protecting glass vial.

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Repr. 1B - Skin Sens. 1

Storage Class Code

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

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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In vitro mouse spermatogenesis with an organ culture method in chemically defined medium.
Sanjo H, et al.
PLoS ONE, 13 (2018)
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)
Yuanchao Li et al.
The journal of headache and pain, 17, 49-49 (2016-05-07)
As a complex nervous system disease, migraine causes severe healthy and social issues worldwide. Valproate (VPA) is a widely used treatment agent against seizures and bipolar disorder, and its function to alleviate damage due to migraine has also been verified
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)
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)
View All Related Papers

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.

Protocols

HPLC Analysis of Vitamins, Fat Soluble (A and E), on SUPELCOSIL™ LC-18

Separation of δ-Tocopherol, analytical standard; Retinyl acetate; (+)-γ-Tocopherol; α-Tocopherol, ≥95.5%; Retinol; Vitamin A (acetate), meets USP testing specifications

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