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Procyanidin B3

February 15, 2024

Procyanidin B3 is a B type proanthocyanidin. Procyanidin B3 is a catechin dimer (catechin-(4α→8)-catechin).

Procyanidin B3
Names
IUPAC name
[(2R,3S,4S)-Flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3S)-flavan-3,3′,4′,5,7-pentol]
Systematic IUPAC name
(2R,2′R,3S,3′S,4S)-2,2′-Bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-2H,2′H-[4,8′-bi-1-benzopyran]-3,3′,5,5′,7,7′-hexol
Other names
Procyanidin B3
Identifiers
  • 23567-23-9 N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:75630
ChEMBL
  • ChEMBL501490
ChemSpider
  • 129476
ECHA InfoCard 100.150.578
EC Number
  • 621-754-2
  • 146798
UNII
  • 2TC1A0KEAQ
  • DTXSID60178193
  • InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1
    Key: XFZJEEAOWLFHDH-AVFWISQGSA-N
  • O[C@H]1Cc2c(O)cc(O)c([C@H]3[C@H](O)[C@H](Oc4cc(O)cc(O)c34)c3ccc(O)c(O)c3)c2O[C@@H]1c1ccc(O)c(O)c1
Properties
C30H26O12
Molar mass 578.52 g/mol
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Natural occurrences edit

It can be found in red wine,[1] in barley,[2][3] in beer,[4] in peach[5] or in Jatropha macrantha, the Huanarpo Macho.[6]

Health effects edit

It has been identified as a hair-growth stimulant.[2]

Chemical synthesis edit

Molar equivalents of synthetic (2R,3S,4R or S)-leucocyanidin and (+)-catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans-[4,8]- and [4,6]-bi-[(+)-catechins] (procyanidins B3, B6) the all-trans-[4,8:4,8]- and [4,8:4,6]-tri-[(+)-catechins] (procyanidin C2 and isomer).[7]

See also edit

References edit

  1. ^ C. Dallas, J.M. Ricardo-Da-Silva and Olga Laureano (1995). (PDF). Vitis. 34 (1): 51–56. Archived from the original (PDF) on 2013-12-03. Retrieved 2013-06-24.
  2. ^ a b Kamimura, A; Takahashi, T (2002). "Procyanidin B-3, isolated from barley and identified as a hair-growth stimulant, has the potential to counteract inhibitory regulation by TGF-beta1". Experimental Dermatology. 11 (6): 532–41. doi:10.1034/j.1600-0625.2002.110606.x. PMID 12473061. S2CID 39454993.
  3. ^ Quinde-Axtell, Zory; Baik, Byung-Kee (2006). "Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration". Journal of Agricultural and Food Chemistry. 54 (26): 9978–84. doi:10.1021/jf060974w. PMID 17177530.
  4. ^ Delcour, Jan (1985). Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer.
  5. ^ Infante, Rodrigo; Contador, Loreto; Rubio, Pía; Aros, Danilo; Peña-Neira, Álvaro (2011). "Postharvest Sensory and Phenolic Characterization of 'Elegant Lady' and 'Carson' Peaches" (PDF). Chilean Journal of Agricultural Research. 71 (3): 445–451. doi:10.4067/S0718-58392011000300016.
  6. ^ Benavides, Angelyne; Montoro, Paola; Bassarello, Carla; Piacente, Sonia; Pizza, Cosimo (2006). "Catechin derivatives in Jatropha macrantha stems: Characterisation and LC/ESI/MS/MS quali–quantitative analysis". Journal of Pharmaceutical and Biomedical Analysis. 40 (3): 639–47. doi:10.1016/j.jpba.2005.10.004. PMID 16300918.
  7. ^ Delcour, Jan. A.; Ferreira, Daneel; Roux, David G. (1983). "Synthesis of condensed tannins. Part 9. The condensation sequence of leucocyanidin with (+)-catechin and with the resultant procyanidins". Journal of the Chemical Society, Perkin Transactions 1: 1711. doi:10.1039/P19830001711.


 

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

February 15, 2024
procyanidin, type, proanthocyanidin, catechin, dimer, catechin, catechin, namesiupac, name, flavan, pentol, flavan, pentol, systematic, iupac, name, dihydroxyphenyl, tetrahydro, benzopyran, hexolother, names, identifierscas, number, 23567, model, jsmol, intera. Procyanidin B3 is a B type proanthocyanidin Procyanidin B3 is a catechin dimer catechin 4a 8 catechin Procyanidin B3 NamesIUPAC name 2R 3S 4S Flavan 3 3 4 5 7 pentol 4 8 2R 3S flavan 3 3 4 5 7 pentol Systematic IUPAC name 2R 2 R 3S 3 S 4S 2 2 Bis 3 4 dihydroxyphenyl 3 3 4 4 tetrahydro 2H 2 H 4 8 bi 1 benzopyran 3 3 5 5 7 7 hexolOther names Procyanidin B3IdentifiersCAS Number 23567 23 9 N3D model JSmol Interactive imageChEBI CHEBI 75630ChEMBL ChEMBL501490ChemSpider 129476ECHA InfoCard 100 150 578EC Number 621 754 2PubChem CID 146798UNII 2TC1A0KEAQCompTox Dashboard EPA DTXSID60178193InChI InChI 1S C30H26O12 c31 13 7 20 37 24 23 8 13 41 29 12 2 4 16 33 19 36 6 12 27 40 26 24 25 21 38 10 17 34 14 9 22 39 28 42 30 14 25 11 1 3 15 32 18 35 5 11 h1 8 10 22 26 29 31 40H 9H2 t22 26 27 28 29 m0 s1Key XFZJEEAOWLFHDH AVFWISQGSA NSMILES O C H 1Cc2c O cc O c C H 3 C H O C H Oc4cc O cc O c34 c3ccc O c O c3 c2O C H 1c1ccc O c O c1PropertiesChemical formula C30H26O12Molar mass 578 52 g molHazardsGHS labelling PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P261 P264 P271 P280 P302 P352 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P403 P233 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Natural occurrences 2 Health effects 3 Chemical synthesis 4 See also 5 ReferencesNatural occurrences editIt can be found in red wine 1 in barley 2 3 in beer 4 in peach 5 or in Jatropha macrantha the Huanarpo Macho 6 Health effects editIt has been identified as a hair growth stimulant 2 Chemical synthesis editMolar equivalents of synthetic 2R 3S 4R or S leucocyanidin and catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all trans 4 8 and 4 6 bi catechins procyanidins B3 B6 the all trans 4 8 4 8 and 4 8 4 6 tri catechins procyanidin C2 and isomer 7 See also editPhenolic content in wineReferences edit C Dallas J M Ricardo Da Silva and Olga Laureano 1995 Degradation of oligomeric procyanidins and anthocyanins in a Tinta Roriz red wine during maturation PDF Vitis 34 1 51 56 Archived from the original PDF on 2013 12 03 Retrieved 2013 06 24 a b Kamimura A Takahashi T 2002 Procyanidin B 3 isolated from barley and identified as a hair growth stimulant has the potential to counteract inhibitory regulation by TGF beta1 Experimental Dermatology 11 6 532 41 doi 10 1034 j 1600 0625 2002 110606 x PMID 12473061 S2CID 39454993 Quinde Axtell Zory Baik Byung Kee 2006 Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration Journal of Agricultural and Food Chemistry 54 26 9978 84 doi 10 1021 jf060974w PMID 17177530 Delcour Jan 1985 Structure elucidation of proanthocyanidins Direct synthesis and isolation from Pilsener beer Infante Rodrigo Contador Loreto Rubio Pia Aros Danilo Pena Neira Alvaro 2011 Postharvest Sensory and Phenolic Characterization of Elegant Lady and Carson Peaches PDF Chilean Journal of Agricultural Research 71 3 445 451 doi 10 4067 S0718 58392011000300016 Benavides Angelyne Montoro Paola Bassarello Carla Piacente Sonia Pizza Cosimo 2006 Catechin derivatives in Jatropha macrantha stems Characterisation and LC ESI MS MS quali quantitative analysis Journal of Pharmaceutical and Biomedical Analysis 40 3 639 47 doi 10 1016 j jpba 2005 10 004 PMID 16300918 Delcour Jan A Ferreira Daneel Roux David G 1983 Synthesis of condensed tannins Part 9 The condensation sequence of leucocyanidin with catechin and with the resultant procyanidins Journal of the Chemical Society Perkin Transactions 1 1711 doi 10 1039 P19830001711 nbsp This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Procyanidin B3 amp oldid 1153512388, wikipedia, wiki, book, books, library,

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