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R7632 Sigma-Aldrich

Retinol

synthetic, ≥95% (HPLC), crystalline

Synonym: Axerophthol, Vitamin A alcohol, Vitamin A, Vitamin A1, all-trans-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol

  • CAS Number 68-26-8

  • Empirical Formula (Hill Notation) C20H30O

  • Molecular Weight 286.45

  •  Beilstein/REAXYS Number 403040

  •  EC Number 200-683-7

  •  MDL number MFCD00001552

  •  eCl@ss 34058018

  •  PubChem Substance ID 24899395

  •  NACRES NA.79

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Properties

Related Categories Antitumor Agents, Biochemicals and Reagents, Cancer Research, Carotenoid, Cell Biology,
Quality Level   200
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

Description

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

1 g in ampule

100, 250, 500 mg in ampule

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.

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
VH6750000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

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

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Vitamins, Fat Soluble (A and E), on SUPELCOSIL™ LC-18
Keywords: Chromatography, High performance liquid chromatography, Vitamins

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

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, apopt...
BioFiles 2008, 3.9, 12.
Keywords: Apoptosis, Cancer, Cell proliferation, Cellular processes, Chromatin immunoprecipitation, Condensations, Degradations, Diseases, Gene expression, Hormones, Immunoprecipitation, Ligands, Metabolism, Oxidations, Phosphorylations, Polymerase chain reaction, Sequences, Teratogens, Transcription, Type, Ubiquitinations, Usage, Vitamins

Peer-Reviewed Papers
15

References

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