Carotenoids and related compounds. Part 37. Stereochemistry and synthesis of capsorubin

Bowden, Roy D.; Cooper, R. D. G.; Harris, Christopher; Moss, G. P.; Weedon, B. C. L.; Jackman, Lloyd M.

doi:10.1039/p19830001465

Cited by 11 publications

(2 citation statements)

References 13 publications

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“…Alloxanthin (1) crystallised from acetone-light petroleum as red needles, m.p. 189-190 "C; &,,,,,(benzene) 495 and 464 nm (E 107000 and 122000); h,,,,(ethanol) 483 and 454 nm; h,,,,(hexane) 480 and 451 nm; v,,,~(CHC13) 3 610, 3460, 2 167w, 1 612,l 600, 1 045, 1 022, and 965 cm-'; 6, see Table 2; o.r.d., see ref.…”

Section: Methodsmentioning

confidence: 99%

Carotenoids and related compounds. Part 38. Synthesis of (3RS,3′RS)-alloxanthin and other acetylenes

Davies¹,

Khare²,

Mallams³

et al. 1984

J. Chem. Soc., Perkin Trans. 1

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The all-trans, g-cis, and 9,9'-di-cis forms of (3RS,3'RS) -alloxanthin have been synthesised, also the 9cis-isomer of (3RS,6'RS) -crocoxanthin. Perhydrogenation of alloxanthin gives a product with the same optical properties as perhydrozeaxanthin. These results confirm the formulation of alloxanthin as ( 3R,3'R) -7,8,7',8'tetrade hydrop, pcarotene -3,3'-d i 01, of d iatoxant hi n as (3R,3'R) -7,8 -dide hydro -P,P-carotene-3,3'-diol, of crocoxanthin as an enantiomer (probably 3R) of (G'R)-7,8-didehydro-p,~c a rote n -3o I, of m o n ad oxa n t h i n as a n a I Itransi so m er of 7,8d id e h y d ro -P,Eca ro t e n e -3,3'd i o I, a n d of pectenolone as an all-trans-isomer of 3,3'-dihydroxy -7',8'-didehydro-P,P-caroten-4-one. Carotenoid isomers with the cis-configuration about the acyclic double bond adjacent to an acetylenic linkage in either the 7-or 7'-position were shown to be thermodynamically more stable than the all-trans-forms. Alloxanthin, crocoxanthin, and monadoxanthin were isolated from flagellates of the algal class C r y p t ~p h y c e a e , ~. ~ and provided the first examples of natural acetylenic c a r ~t e n o i d s . ~ Alloxanthin was subsequently shown ' to be identical with pectenoxanthin from the scallop Pecten rna~irnus,~*~ with cynthiaxanthin from the tunicate, Halocynthia papillosa,6-8 and with a carotenoid present in the edible mussel, Mytilus edulis, and the California sea mussel, M . californiunus.'Alloxanthin was formulated as the 7,7'-diacetylenic analogue$ of zeaxanthin (8), largely on the basis of its n.m.r. and mass ~p e c t r a . ~The i.r. absorption due to the carbon-carbon triple bond stretching frequency was surprisingly weak, presum-ably owing to the nature of the substitution. Its perhydroderivative (see Experimental section) exhibited similar optical rotation to that of perhydro-zeaxanthin, indicating the 3R,3'R configuration ( ' O Crocoxanthin, monadoxanthin, and pectenolone (a minor pigment from P. maximus and H . papillosa ') were similarly formulated as the mono-acetylenic analogues (3), (4), and (5) of a-cryptoxanthin (9), lutein (lo), and adonixanthin (1 l), respecti ~e l y . ~. ' Diatoxanthin, a common pigment of diatoms '' and Chrysophyceae,' 2, ' was formulated as the mono-acetylenic analogue (6) of zeaxanthin (8), and assigned the 3R,3'R configuration (7) on the basis of 0.r.d. studies.

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Section: Methodsmentioning

confidence: 99%

Carotenoids and related compounds. Part 38. Synthesis of (3RS,3′RS)-alloxanthin and other acetylenes

Davies¹,

Khare²,

Mallams³

et al. 1984

J. Chem. Soc., Perkin Trans. 1

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“…In 1983, their syntheses were investigated but required the collaboration of the research groups of Rüttimann and Weedon to be successful. [103][104] Proof that paprika could react with the diphenyliodonium salt (Iod1) was demonstrated during the photolysis experiments of the papikra/4-(2-methylpropyl)phenyl iodonium hexafluorophosphate (Iod2) combination. A fast photobleaching could be observed within 50 s in toluene upon light irradiation with a Xe lamp.…”

Section: A) B)mentioning

confidence: 99%

Photoinitiators of polymerization with reduced environmental impact: Nature as an unlimited and renewable source of dyes

Noirbent

Dumur

2021

European Polymer Journal

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The development of new procedures aiming at reducing the environmental impact of polymerization processes is a major societal issue. In this field, light-assisted polymerization and especially visible light photopolymerization can address this issue by enabling in the future, Sun, to be used as the irradiation source. Presently, numerous visible light photoinitiators (xanthene dyes, porphyrins and phthalocyanines) are used in industry but their toxicities constitute a major issue for future uses of polymers. Therefore, photopolymerization is facing a short-term challenge and the development of visible light photoinitiators of polymerization has become a blooming field of research during the last decade. An ever-growing effort is thus done to develop new structures, effort which is also supported by the recent applications of photopolymerization in 3D-printing. Depending on the applications, use of synthetic photoinitiators can constitute a severe limitation for future applications of photopolymers so that the use of natural products has been identified as a promising alternative to address the toxicity or the biocompatibility issues. In this review, an overview of the different visible-light photoinitiators based on natural products is provided.

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ChemInform Abstract: Carotenoids and Related Compounds. Part 37. Stereochemistry and Synthesis of Capsorubin (X).

Bowden¹,

VOOPER²,

Harris³

et al. 1983

Chemischer Informationsdienst

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Carotenoids and related compounds. Part 37. Stereochemistry and synthesis of capsorubin

Cited by 11 publications

References 13 publications

Carotenoids and related compounds. Part 38. Synthesis of (3RS,3′RS)-alloxanthin and other acetylenes

Carotenoids and related compounds. Part 38. Synthesis of (3RS,3′RS)-alloxanthin and other acetylenes

Photoinitiators of polymerization with reduced environmental impact: Nature as an unlimited and renewable source of dyes

ChemInform Abstract: Carotenoids and Related Compounds. Part 37. Stereochemistry and Synthesis of Capsorubin (X).

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