Retinol Product Information

RETINOL ALL TRANS
Sigma Prod. No. R7632
CAS NUMBER: 68-26-8
SYNONYMS: Vitamin A; Vitamin A1; Vitamin A Alcohol;

Anti-Infective Vitamin; Axerophthol1
PHYSICAL DESCRIPTION:
Appearance: Yellow to orange with a brown CH3 CH3

cast powder H3C CH3
Molecular weight: 286.5
Formula: C20H30O OH
Melting point: 62-64°C (solvent free)4
EM(325nm) = 52,480 (ethanol)3
CH3
E1%(324-325nm) = 1835 (ethanol)4
RE exhibits fluorescence properties with

maximum absorbance and emission at 325
nm and 520 nm (cyclohexane), respectively.5
METHOD OF PREPARATION:
Retinol all trans (RE) is synthetically prepared by Sigma. Many procedures have been reported for methods of
synthesis which include synthesis from retinal8 and total synthesis from various starting compounds.4,9 Methods of
purification and various assays for purity determination have been described. 4,10
STABILITY / STORAGE AS SUPPLIED:
RE is expected to be stable for about one year if unopened in the sealed amber glass vial (packaged under argon
atmosphere), stored at -20°C. 2
SOLUBILITY / SOLUTION STABILITY:
RE is practically insoluble in water or glycerol. It is soluble in absolute ethanol, methanol, chloroform, ether, fats and
oils.7 RE has been dissolved at 50 mg/ml in chloroform; a clear yellow to orange solution results.2 Stock solutions of
RE (1 mg/ml) were prepared in ethanol, diluted in DMSO under low light conditions and stored at -50°C under nitrogen
in brown glass vials.11 RE solutions (50 µM) were sterile filtered before use. 11 RE both as a solid and in solution is
readily oxidized in air and inactivated by UV light.
RETINOL ALL TRANS
SOLUBILITY / SOLUTION STABILITY: (continued)
To reduce photodestruction of RE, manipulations of RE solutions can be performed under yellow or red
light.12,13 Solutions may be stabilized by dissolving in oil, by the addition of anti-oxidant compounds
including a-tocopherol or hydroquinone or by conversion to the palmitate and acetate esters.3 It is
recommended to prepare solutions fresh for optimal quality. However, if absolutely necessary, store
solutions in the dark under an inert atmosphere at least at -20°C preferably at -70°C. Solvents preferred for
storage are peroxide-free ethyl ether, acid-free acetone or ethyl acetate. For short term storage, ethanol is
suitable as a solvent for spectroscopic analysis.4
USAGE / APPLICATIONS:
The isolation of retinol from human plasma has been described. 14 RE is an effective antioxidant displaying
lipoperoxy radical scavenging activity.15 The interactions between RE and Vitamin E (a-tocopherol) in
suppressing lipid peroxidation were observed in bovine retinal membrane preparations.13 RE may influence
the production of transition vesicles by stimulating the activity of a protein disulfide isomerase-like activity
involved in vesicle formation. 12 RE may be involved in immune system mechanisms; an RE deficiency will
depress the immune response producing a negative effect on both humoral and cellular immunity.16 RE (10
µM) and other retinoid compounds effectively induced sanguinarine and chelerythrine (benzophenanthridine
alkaloids) accumulation in suspension-cell cultures of Sanguinaria canadensis in a way similar to fungal
elicitation. 11 RE (10 µM) stimulated DNA synthesis and possibly repair mechanisms in Sertoli cells of rat.17
GENERAL NOTES:
The USP unit of vitamin A (same as the International Unit6) is equal to 0.3 µg of the pure all-trans isomer of
retinol which is equivalent to 0.344 µg of all-trans retinyl acetate. 7
RE and its metabolites, including retinoic acid, are part of the retinoid class of compounds, involved in
vision, normal embryo morphogenesis and in the regulation of proliferation and differentiation of a number of
cell types. Current information and hypotheses on the absorption, transport, storage and metabolism of this
fat soluble Vitamin A (retinol) have been reviewed. 18 Studies on RE metabolism including its mobilization
and transport in plasma and in tissues via serum and cytosolic retinol-binding proteins have been
described. 19
REFERENCES:
1. Sigma Material Safety Data Sheet

2. Sigma Quality Control Data
3. Dawson, R.M.C. et al., eds. Data for Biochem. Res. 3rd edition, Clarendon Press, Oxford, 136,
1987.
R7632 Page 2 of 3
10/14/96 - ARO
RETINOL ALL TRANS
REFERENCES: (continued)
4. Specifications and Criteria for Biochemical Compounds, 3rd edition, National Academy of Sciences,
78, (1984).
5. Radda, G.K. and Smith, D.S., FEBS Letters, 9, 287, (1970).
6. Martindale, The Extra Pharmacopoeia, 30th ed., 1051, (1993).
7. The Merck Index, 12th edition, #10150, p. 1709.
8. Wendler, N.L. et al., J. Am. Chem. Soc. 72, 234, (1950).
9. Mukaiyama, T. and Ishida, A., Chem. Letters. 1201, (1975).
10. Kofler, M. and Rubin, S.H., Vitamins, Hormones 18, 315, (1960).
11. Mahady, G.B. and Beecher, C.W.W., Natural Product Letters, 8, 173, (1996).
12. Jacobs, E. et al., Life Sciences, 59, 273, (1996).
13. Tesoriere, L. et al., Biochem. Mol. Biol. Int. 37, 1, (1995).
14. Dueker, S.R. et al., Anal. Chem. 66, 4177, 1994.
15. Livrea, M.A. and Tesoriere, L., Methods in Enzymology, 234, 7401, (1994).
16. Chytil, F.J., Nutr. Immunol., 4, 35, (1995).
17. Moreira, J.C.F. et al., Med. Sci. Res. 24, 383, (1996).
18. Blomhoff, R. et al., Science, 250, 399, (1990).
19. Goodman, D.S., Federation Proc., 39, 2716, (1980).
Additional References:
Sebrell, W.H. and Harris, R.S. (eds) The Vitamins, Vol. 1, Academic Press, NY, 2nd ed., 1967 - descriptive
information on the chemistry, physicochemical properties and physiology of Vitamin A.
Morre, D.M. "Intracellular Actions of Vitamin A" Intl. Rev. Cyt. 135, 1, 1992.
R7632 Page 3 of 3
10/14/96 - ARO

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RETINOL ALL TRANS

Sigma Prod. No. R7632

CAS NUMBER: 68-26-8

SYNONYMS: Vitamin A; Vitamin A1; Vitamin A Alcohol;

Appearance: Yellow to orange with a brown CH3 CH3

RE exhibits fluorescence properties with

STABILITY / STORAGE AS SUPPLIED:

SOLUBILITY / SOLUTION STABILITY:

SOLUBILITY / SOLUTION STABILITY: (continued)

1. Sigma Material Safety Data Sheet

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