Studies in the polyene series. Part L. “Anhydrovitamin A<sub>2</sub>”

Henbest, H. B.; Jones, E. R. H.; Owen, Terence C.; Thaller, V.

doi:10.1039/jr9550002763

Cited by 14 publications

(13 citation statements)

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“…Moreover, examination of the i.r. spectrum of this anhydrovitamin A2 prepared from 3-hydroxyvitamin A shows a sharp band at llOOcm.-l assigned to an ether group (Henbest, Jones, Owen & Thaller, 1955).…”

Section: Discussionmentioning

confidence: 93%

Oxidation of zeaxanthin. Isolation and properties of 3-hydroxyretinene

Barua¹,

Barua²

1966

Biochemical Journal

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1. Anthers of Delonix regia flowers are a rich source of zeaxanthin. 2. Oxidation of zeaxanthin with hydrogen peroxide in the presence of osmium tetroxide results in the formation of 3-hydroxyretinene as one of the products. 3. 3-Hydroxyretinene gives 3-acetoxyretinene with acetic anhydride, and an oxime with hydroxylamine hydrochloride. 4. Reduction of 3-hydroxyretinene with sodium borohydride yields 3-hydroxyvitamin A. 5. Treatment of 3-hydroxyvitamin A with dry ethanolic hydrogen chloride results in the formation of 3-ethoxyanhydrovitamin A (anhydrovitamin A(2)) and a compound that resembles naturally occurring anhydrovitamin A(2).

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Section: Discussionmentioning

confidence: 93%

Oxidation of zeaxanthin. Isolation and properties of 3-hydroxyretinene

Barua¹,

Barua²

1966

Biochemical Journal

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“…-< -1 -\>> -4 /CH2. -apo-12'-carotenol retro-3-Dehydroretinyl acetate (compound II) Compound (IV) Reference Oroshnik et al (1952) Oroshnik et al (1952) Shantz (1950 Hawkins & Hunter (1944) Ruiegg et al (1959) Present work Henbest et al (1955a) 3-dehydroretinyl acetate clearly indicate that it possesses one double bond fewer than compound (IV).…”

Section: Ch20ococh3 (I)mentioning

confidence: 83%

“…By the reaction of anhydrovitamin A1 with N-bromosuccinimide and subsequent dehydrobromination, Henbest et al (1955a) isolated a compound (compound IV) exhibiting a main absorption maximum at 408m,u with subsidiary maxima at 387 and 433m,. The absorption maxima of the hydrobromic acid reaction product of -~---…”

Section: Tracesmentioning

confidence: 99%

“…Vitamin A compounds possessing the retro system of conjugated double bonds have been encountered in biological samples (Balasundaram, Bamji, Cama, Sundaresan & Varma, 1958;Varma, Erdody & Murray, 1965a). The structure of the naturally occurring anhydrovitamin A2 was shown to be 3-hydroxyanhydrovitamin A1 (Barua & Nayar, 1966), whereas the chemically synthesized anhydrovitamin A2 was 3-ethoxyanhydrovitamin A1 (Henbest, Jones, Owen & Thaller, 1955a). When chemically synthesized anhydrovitamin A2 was fed to vitamin A-deficient rats, it gave rise to 'rehydrovitamin A2' (Balasundaram et al 1958;Bamji, Cama & Sundaresan, 1962).…”

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confidence: 99%

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Preparation, properties and metabolism of retro-3-dehydroretinyl acetate

Mallia

Lakshmanan

John

et al. 1968

Biochemical Journal

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1. Treatment of 3-dehydroretinyl acetate with aqueous hydrobromic acid resulted in the formation of retro-3-dehydroretinyl acetate, which, on alkaline hydrolysis, gave the corresponding alcohol. 2. retro-3-Dehydroretinyl acetate was isomerized to 3-dehydrovitamin A when fed to vitamin A-deficient rats. 3. When retro-3-dehydroretinyl acetate was administered orally, it was hydrolysed to retro-3-dehydroretinol in the rat intestine, isomerized to 3-dehydroretinol and esterified before being transported to the liver for storage. 4. When administered intraperitoneally, both 3-dehydrovitamin A and retro-3-dehydrovitamin A were accumulated in liver and other tissues, whereas after enterectomy 3-dehydrovitamin A was not detected anywhere in the body. 5. The small intestine was shown to be the major site of conversion of retro-3-dehydrovitamin A into 3-dehydrovitamin A. 6. The extent of conversion of retro-3-dehydroretinyl acetate into 3-dehydrovitamin A was much smaller than that of the conversion of retro-retinyl acetate into vitamin A. 7. The biological potency of retro-3-dehydroretinyl acetate, determined by the rat-growth assay, was 2.6% of that all-trans-retinyl acetate, when given orally.

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“…The allylic hydroxy group of 19 suggested that this compound might be epoxidized in a selective way. Cyclohexenols are known to be epoxidized cis to the hydroxy group [29] due to H-bonding between the hydroxyl and the peracid. In openchain allyl alcohols selectivity is only expected when a certain conformation is preferred over others in the transition state.…”

Section: C)mentioning

confidence: 99%

Determination of the Relative Configurations in the Side Chains of the Antibiotics Hedamycin and Pluramycin A; Synthesis and NMR. Data of Suitable Model Compounds

Ceroni

Séquin

1982

Helvetica Chimica Acta

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Several diepoxyhexanoates and epoxyhexenoates were prepared by epoxidation of methyl 2‐methyl‐2,4‐hexadienoate or by Darzens condensation. Their 1 H‐ and 13C‐NMR. spectra were measured and assigned. Comparison of these data with the spectra of the antibiotics hedamycin (1) and pluramycin A (2) allowed the determi‐nation of the relative configurations in the side chains of these antibiotics. They were found to be (14R*,16S*,17R*,18S*) for hedamycin (1) and (14R*,16S*,17Z) for pluramycin A (2).

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Studies in the polyene series. Part L. “Anhydrovitamin A₂”

Cited by 14 publications

References 0 publications

Oxidation of zeaxanthin. Isolation and properties of 3-hydroxyretinene

Oxidation of zeaxanthin. Isolation and properties of 3-hydroxyretinene

Preparation, properties and metabolism of retro-3-dehydroretinyl acetate

Determination of the Relative Configurations in the Side Chains of the Antibiotics Hedamycin and Pluramycin A; Synthesis and NMR. Data of Suitable Model Compounds

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Studies in the polyene series. Part L. “Anhydrovitamin A2”

Cited by 14 publications

References 0 publications

Oxidation of zeaxanthin. Isolation and properties of 3-hydroxyretinene

Oxidation of zeaxanthin. Isolation and properties of 3-hydroxyretinene

Preparation, properties and metabolism of retro-3-dehydroretinyl acetate

Determination of the Relative Configurations in the Side Chains of the Antibiotics Hedamycin and Pluramycin A; Synthesis and NMR. Data of Suitable Model Compounds

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Studies in the polyene series. Part L. “Anhydrovitamin A₂”