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Procyanidin C1 information


Procyanidin C1
Chemical structure of procyanidin C1
Names
IUPAC name
[(2R,3R,4R)-Flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3R,4S)-flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3R)-flavan-3,3′,4′,5,7-pentol]
Systematic IUPAC name
(12R,13R,14R,22R,23R,24S,32R,33R)-12,22,32-Tris(3,4-dihydroxyphenyl)-12H,22H,32H-[14,28:24,38-ter-1-benzopyran]-13,15,17,23,25,27,33,35,37-nonol
Other names
Procyanidin C1
Procyanidol C1
Epicatechin-(4.beta.-->8)epicatechin-(4.beta.-->8)epicatechin
Epicatechin-(4β→8)-epicatechin--(4β→8)-epicatechin
Identifiers
CAS Number
  • 37064-30-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:75643
ChEMBL
  • ChEMBL290632
ChemSpider
  • 148540
KEGG
  • C17624
PubChem CID
  • 169853
UNII
  • 33516LCW4F checkY
CompTox Dashboard (EPA)
  • DTXSID10190562 Edit this at Wikidata
InChI
  • InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1
    Key: MOJZMWJRUKIQGL-XILRTYJMSA-N
  • InChI=1/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1
    Key: MOJZMWJRUKIQGL-XILRTYJMBW
SMILES
  • c1cc(c(cc1[C@@H]2[C@@H](Cc3c(cc(c(c3O2)[C@H]4c5c(cc(c(c5O[C@@H]([C@@H]4O)c6ccc(c(c6)O)O)[C@H]7c8c(cc(cc8O[C@@H]([C@@H]7O)c9ccc(c(c9)O)O)O)O)O)O)O)O)O)O)O
Properties
Chemical formula
C45H38O18
Molar mass 866.77 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Procyanidin C1 (PCC1) is a B type proanthocyanidin. It is an epicatechin trimer found in grape (Vitis vinifera),[1] unripe apples,[2] and cinnamon.[3]

  1. ^ Proanthocyanidin composition of red Vitis vinifera varieties from the Douro valley during ripening : Influence of cultivation altitude. Mateus Nuno, Marques Sara, Goncalves Ana C., Machado José M. and De Freitas Victor, American journal of enology and viticulture, 2001, vol. 52, no2, pp. 115-121, INIST 1129642
  2. ^ Nakano, Nobuhiro; Nishiyama, Chiharu; Tokura, Tomoko; Nagasako-Akazome, Yoko; Ohtake, Yasuyuki; Okumura, Ko; Ogawa, Hideoki (2008-07-02). "Procyanidin C1 from Apple Extracts Inhibits FcεRI-Mediated Mast Cell Activation". International Archives of Allergy and Immunology. 147 (3): 213–221. doi:10.1159/000142044. ISSN 1018-2438. PMID 18594151. S2CID 43866026. Retrieved 2022-02-20.
  3. ^ Sun, Peng; Li, Kai; Wang, Ting; Ji, Jun; Wang, Yan; Chen, Kai-Xian; Jia, Qi; Li, Yi-Ming; Wang, He-Yao (2019-07-23). "Procyanidin C1, a Component of Cinnamon Extracts, Is a Potential Insulin Sensitizer That Targets Adipocytes". Journal of Agricultural and Food Chemistry. 67 (32). American Chemical Society (ACS): 8839–8846. doi:10.1021/acs.jafc.9b02932. ISSN 0021-8561. PMID 31334651. S2CID 198169719.

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Procyanidin C1

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Procyanidin C1 (PCC1) is a B type proanthocyanidin. It is an epicatechin trimer found in grape (Vitis vinifera), unripe apples, and cinnamon. Procyanidin...

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Procyanidin

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chronic disorders. A type proanthocyanidin B type proanthocyanidin Procyanidin C1 Procyanidin C2 Tannin Polyphenol Phenolic compounds in wine Souquet, J; Cheynier...

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Procyanidin C2

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Procyanidin C2 is a B type proanthocyanidin trimer, a type of condensed tannin. Procyanidin C2 is found in grape seeds (Vitis vinifera) and wine, in barley...

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Senolytic

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Li Z, Liu H, Wang Y, Lin X, et al. (December 2021). "The flavonoid procyanidin C1 has senotherapeutic activity and increases lifespan in mice". Nature...

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Procyanidin B2

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Procyanidin B2 is a B type proanthocyanidin. Its structure is (−)-Epicatechin-(4β→8)-(−)-epicatechin. Procyanidin B2 can be found in Cinchona pubescens...

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2021 in science

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and packaging. 6 December Scientists show that and how the flavonoid Procyanidin C1 of the antioxidant grape seed extract increases the health- and lifespan...

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Phenolic content in wine

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Oligomeric procyanidins : Procyanidin B1 Procyanidin B2 Procyanidin B3 Procyanidin B4 B1-3-O-gallate B2-3-O-gallate B2-3'-O-gallate procyanidin C1...

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Procyanidin B1

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Procyanidin B1 is a procyanidin dimer. It is a molecule with a 4→8 bond (epicatechin-(4β→8)-catechin). Proanthocyanidin-B1 can be found in Cinnamomum...

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Procyanidin A2

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Procyanidin A2 is an A type proanthocyanidin. It is found in avocado, chestnut, cranberry juice concentrate, lychee fruit pericarp, peanut skins, Cinchona...

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B type proanthocyanidin

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be synthesized with procyanidin-rich grape seed extracts reacted with flavan-3-ols under acid catalysis. Procyanidin C1 Procyanidin C2 A stereoselective...

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Timeline of aging research

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of healthy body weight. Scientists show that and how the flavonoid Procyanidin C1 of the antioxidant grape seed extract increases the health- and lifespan...

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Procyanidin B8

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Procyanidin B8 is a B type proanthocyanidin. Procyanidin B8 is a catechin-(4α→6)-epicatechin dimer. It can be found in grape seeds and in beer. Procyanidin...

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Procyanidin B5

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Procyanidin B5 is a B type proanthocyanidin. Procyanidin B5 is an epicatechin-(4β → 6)-epicatechin dimer. It can be found in grape seeds, in Hibiscus cannabinus...

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C45H38O18

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Procyanidin B3

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Procyanidin B3 is a B type proanthocyanidin. Procyanidin B3 is a catechin dimer (catechin-(4α→8)-catechin). It can be found in red wine, in barley, in...

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Procyanidin B4

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Procyanidin B4 is a B type proanthocyanidin. Procyanidin-B4 is a catechin-(4α→8)-epicatechin dimer. It is found in the litchi pericarp, in grape seeds...

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C2

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nerve 2 Chlorophyll c2, a form of chlorophyll Complement component 2 Procyanidin C2, a plant phenolic compound Prodelphinidin C2, a plant phenolic compound...

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Arecatannin

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Arecatannins are a class of condensed tannins in the sub-class procyanidins contained in the seeds of Areca catechu also called betel nut. The arecatannin-type...

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Oenin

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cation and copigmentation with the Z-chalcone form. In the presence of procyanidin C2, the red color of oenin appears more stable. However, the HPLC chromatogram...

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Leucocyanidin

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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). Leucocyanidin...

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Cinnamtannin B1

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Oc1cc(O)c2c(c1)O[C@@]1([C@@H]([C@H]2c2c(O1)cc(c1c2O[C@H](c2ccc(c(c2)O)O)[C@@H]([C@H]1c1c(O)cc(c2c1O[C@@H]([C@@H](C2)O)c1ccc(c(c1)O)O)O)O)O)O)c1ccc(c(c1)O)O Properties...

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Naturally occurring phenols

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Weixing; Miller, Jack M. (2003). "Tandem mass spectrometry of the B-type procyanidins in wine and B-type dehydrodicatechins in an autoxidation mixture of (+)-catechin...

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