all-trans Retinal CAS 116-31-4

CAS Number

116-31-4

Grade

Highly Purified

Molecular Formula

C20H28O

Molecular Weight

284.44

EU Commodity Code

38220090

Shipping Temp

Storage Temp

-70°C

(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal; all -trans-Vitamin A Aldehyde; Retinene; Retinylaldehyde

Corotenoid component of the visual pigments. All-trans retinal is converted to retinoic acid in vivo by the action of retinal dehydrogenase.

Retinal is also known as retinaldehyde. It was originally called retinene,[2] and renamed[3] after it was discovered to be vitamin A aldehyde.[4][5] Retinal is one of the many forms of vitamin A (the number of which varies from species to species). Retinal is a polyene chromophore, bound to proteins called opsins, and is the chemical basis of animal vision. Retinal allows certain microorganisms to convert light into metabolic energy.

Vertebrate animals ingest retinal directly from meat, or they produce retinal from carotenoids, either from one of two carotenes (α-carotene, β-carotene) or from β-cryptoxanthin, a type of xanthophyll. These carotenoids must be obtained from plants or other photosynthetic organisms. No other carotenoids can be converted by animals to retinal, and some carnivores cannot convert any carotenoids at all. The other main forms of vitamin A, retinol, and a partially active form, retinoic acid, may both be produced from retinal.

Invertebrates such as insects and squid use hydroxylated forms of retinal in their visual systems, which derive from conversion from other xanthophylls.

Melting Point

60-63ºC

Solubility

Chloroform (Slightly), Methanol (Slightly)

Atmosphere

Inert Gas

Method for Determining Identity

Proton NMR (CDCl3) Spectroscopic analysis and Mass Spectrometric analysis

TLC Conditions

SiO2; Hexane: Ethyl Acetate; 8:2; Visualized with UV, AMCS, and Naked Eye; Rf=0.55

Storage and Stability

Aliquot to avoid repeated freezing and thawing and store at -70°C. Aliquots are stable for 6 months after receipt. For maximum recovery of product, centrifuge the original vial after thawing and prior to removing the cap. Light and temperature sensitive. Store under inert atmosphere.

Important Note

This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.

Toxicity and Hazards: All products should be handled by qualified personnel only, trained in laboratory procedures.

Source

Synthetic

Purity

~95%

Form

Supplied as a dark yellow solid

Important Note

This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.

References

1. Merck Index, 13th Edition, 8249|2. WALD, GEORGE (14 July 1934). "Carotenoids and the Vitamin A Cycle in Vision". Nature. 134 (3376): 65–65. doi:10.1038/134065a0.|3. Wald, G (11 October 1968). "Molecular basis of visual excitation.". Science. 162 (3850): 230–9. PMID 4877437. doi:10.1126/science.162.3850.230.|4. MORTON, R. A.; GOODWIN, T. W. (1 April 1944). "Preparation of Retinene in Vitro". Nature. 153 (3883): 405–406. doi:10.1038/153405a0.|5. BALL, S; GOODWIN, TW; MORTON, RA (1946). "Retinene1-vitamin A aldehyde.". The Biochemical Journal. 40 (5-6): lix. PMID 20341217.|6. Ball, et al.: Biochem. J., 42, 516 (1948)|7. O’Brien, D.F., et al.: Science, 218, 961 (1982)

USBio References

No references available

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R1659-04 all-trans Retinal (Vitamin A Aldehyde, Retinene, Retinylaldehyde) CAS: 116-31-4

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Grade

Molecular Formula

Molecular Weight

EU Commodity Code

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(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal; all -trans-Vitamin A Aldehyde; Retinene; Retinylaldehyde

References

USBio References

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