95144

Sigma-Aldrich

Retinol

BioXtra, ≥97.5% (HPLC), ~3100 U/mg

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:

Quality Level

biological source

synthetic

product line

BioXtra

assay

≥97.5% (HPLC)

form

powder

specific activity

~3100 U/mg

shelf life

limited shelf life

color

faint yellow to very dark yellow

mp

56-61 °C
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.

Application

Retinol has been used:
  • as a standard in peak identification and quantification in reverse phase HPLC
  • as a standard to estimate the concentration of vitamin A
  • to study the inhibitory effect of retinol on murine norovirus (MNV) replication in murine RAW 264.7 cells
  • as a component in the reaction mixture for the lecithin:retinol acyltransferase (LRAT) assay

Biochem/physiol Actions

Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain.
Retinol is biological active in a wide range of processes.
It is not biologically active and works as a precursor of active retinoids. Retinol is converted to retinaldehyde and subsequently to retinoic acid.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Unit Definition

1 U corresponds to 1 international U acc. to Ph Eur II, 217 (1983)

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

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(6), 421-430 (2003)
Retinyl palmitate does not have an adjuvant effect on the antibody response of chicks to keyhole limpet hemocyanin regardless of vitamin A status
Livingston KA and Klasing KC
Poultry Science, 90(5), 965-970 (2011)
Antiviral effect of vitamin A on norovirus infection via modulation of the gut microbiome
Lee H and Ko G
Scientific reports, 25835-25835 (2016)
Heetae Lee et al.
Scientific reports, 6, 25835-25835 (2016-05-18)
The effect and underlying mechanism of vitamin A on norovirus infection are largely unknown. This study aimed to investigate how vitamin A administration affects the gut microbiome after norovirus infection. Here, we demonstrate that treatment with either retinol or retinoic...
Responses of blood metabolites and proteins to different vitamin A levels in Korean native steers.
Wang T, et al.
Pakistan journal of botany, 34(4) (2014)
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

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