503. Studies in the polyene series. Part XLIII. The structure and synthesis of vitamin A2 and related compounds

Farrar, Kathleen R.; Hamlet, J. C.; Henbest, H. B.; Jones, E. R. H.

doi:10.1039/jr9520002657

Cited by 45 publications

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“…Similar treatment of 3-dehydroretinol (3,4-didehydroretinol) with ethanolic HCI gives anhydrovitamin A2, exhibiting similar absorption bands in the u.v. region (Shantz, 1948;Farrar et al, 1952). Further studies by Henbest et al (1955) have shown that anhydrovitamin A2 may have a 3-ethoxyanhydroretinol or 3-methoxyanhydroretinol structure, depending on the nature of the solvent used in its preparation.…”

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Structure and synthesis of naturally occurring anhydrovitamin A2

Barua¹,

Verma²,

Das³

1979

Biochemical Journal

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The structure of naturally occurring anhydrovitamin A2 was elucidated as 3-hydroxyanhydroretinol from study of its u.v.--visible, i.r., n.m.r. and mass spectra. The structure has been confirmed by a chemical synthesis. Saccobranchus fossils, a freshwater fish, can convert 3-hydroxyretinol into 3-hydroxyanhydroretinol, which in turn is converted into-3-dehydroretinol. Chemical conversion of 3-hydroxyretinol into 3-dehydroretinol was also carried out.

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mentioning

confidence: 99%

Structure and synthesis of naturally occurring anhydrovitamin A2

Barua¹,

Verma²,

Das³

1979

Biochemical Journal

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Comparative embryolethality and teratogenicity of the all‐ trans isomers of retinoic acid, 3,4‐didehydroretinyl acetate, and retinyl acetate in pregnant rats

Duitsman

Olson

1996

Teratology

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The teratogenic potencies of the all‐trans isomers of retinoic acid (RA), 3,4‐didehydroretinyl acetate (A2), and retinyl acetate (A1) were compared. Groups of eight timed‐pregnant Sprague‐Dawley rats were administered single equimolar doses (3.5–352 μmol/kg BW) of the retinoids orally in oil on day 8.5 of pregnancy, and dams and fetuses were sacrificed on day 19. The relative teratogenicity and embryolethality of the three tested retinoids were: RA > A2 > A1. The no‐effect level of RA and A2 was 3.5 μmol/kg BW and of A1 was 35 μmol/kg BW. Whereas the adverse effects of RA and A1 were dose dependent, A2 showed biphasic effects, with a peak of embryolethality at 35 μmol/kg BW. Dams also exhibited weight loss and other toxic manifestations from doses of A2 and RA ≥ 35 μmol/kg BW. In dosed dams, (1) Liver concentrations of A1 and A2 increased with the doses of A1 and A2, respectively, (2) RA had little effect on liver A1 except for an increase at the highest toxic dose, and (3) A2 showed a sparing effect on liver A1. RA, although not detected in fetuses from dams treated with A1, was present in significant concentrations (0.5–4.1 nmol/g liver) in fetuses from dams treated with A2. The biphasic change in embryolethality with the dose of A2 correlates with this enhanced concentration of fetal RA. We hypothesize that the actual teratogen in the fetuses of A2‐dosed dams is RA. A2 might induce this biphasic effect by inhibiting the catabolism of RA at lower doses and its formation at higher doses. © 1996 Wiley‐Liss, Inc.

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