Digallic acid: Difference between revisions

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Revision as of 07:14, 28 September 2011 editحسن علي البط (talk \| contribs)Extended confirmed users, Pending changes reviewers19,940 edits added Category:Trihydroxybenzoic acids using HotCat ← Previous edit		Latest revision as of 20:37, 19 December 2023 edit undoJWBE (talk \| contribs)Extended confirmed users10,127 edits −Category:Vinylogous carboxylic acids; ±Category:Pyrogallols→Category:Gallate esters using HotCat
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	{{~~chembox~~		{{Chembox
			\| Verifiedfields = changed
	\| Watchedfields = changed		\| Watchedfields = changed
	\| verifiedrevid = ~~401013811~~		\| verifiedrevid = 441307529
	\| ImageFile = Digallic ~~acid~~.svg		\| ImageFile = Digallic Acid Structural Formula V1.svg
	\| ImageSize =		\| ImageSize =
	\| ImageCaption = ~~meta-depside bond digalloyl ester~~		\| ImageCaption =
	\| ~~IUPACName~~ = 3,4-~~dihydroxy~~-5-(3,4,5-trihydroxybenzoyl)~~oxybenzoic~~ acid		\| PIN = 3,4-Dihydroxy-5-benzoic acid
	\| OtherNames = Digallate<br>3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate<br>m-digallic acid<br>Digalloyl ester		\| OtherNames = Digallate<br>3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate<br>m-digallic acid<br>Digalloyl ester
	\| Section1 = {{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| Abbreviations =		\| Abbreviations =
			\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo = 536-08-3		\| CASNo = 536-08-3
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = 404KO0584X
	\| Beilstein =		\| Beilstein =
	\| EINECS =		\| EINECS =
	\| PubChem = 341		\| PubChem = 341
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
			\| ChEMBL = 366356
	\| SMILES = C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)		\| SMILES = C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
⚫	\| ~~InChI~~ =
			\| ChemSpiderID = 334
			\| SMILES2 = O=C(O)c2cc(O)c(O)c(OC(=O)c1cc(O)c(O)c(O)c1)c2
			\| InChI = 1/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)
			\| InChIKey = COVFEVWNJUOYRL-UHFFFAOYAG
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 1S/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = COVFEVWNJUOYRL-UHFFFAOYSA-N
	\| RTECS =		\| RTECS =
	\| MeSHName =		\| MeSHName =
			\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI =		\| ChEBI =
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG =		\| KEGG =
			}}
	\| ATCvet =
		⚫	\|Section2={{Chembox Properties
	\| ATCCode_prefix =
			\| C=14 \| H=10 \| O=9
	\| ATCCode_suffix =
	\| ATC_Supplemental =}}
⚫	\| Section2 = {{Chembox Properties
	\| Formula = C<sub>14</sub>H<sub>10</sub>O<sub>9</sub>
	\| MolarMass = 322.22 g/mol
	\| ExactMass = 322.032481 u
	\| Appearance =		\| Appearance =
	\| Density =		\| Density =
	\| MeltingPt =		\| MeltingPt =
	\| ~~Melting_notes~~ =		\| MeltingPt_notes =
	\| BoilingPt =		\| BoilingPt =
	\| ~~Boiling_notes~~ =		\| BoilingPt_notes =
	\| Solubility =		\| Solubility =
	\| SolubleOther =		\| SolubleOther =
	\| Solvent =		\| Solvent =
	\| pKa =		\| pKa =
	\| pKb = }}		\| pKb =
			}}
	\| Section7 = {{Chembox Hazards		\|Section7={{Chembox Hazards
	\| ~~ExternalMSDS~~ =		\| ExternalSDS =
	\| EUClass =
	\| EUIndex =
	\| MainHazards =		\| MainHazards =
	\| NFPA-H =		\| NFPA-H =
	\| NFPA-F =		\| NFPA-F =
	\| NFPA-R =		\| NFPA-R =
	\| NFPA-O =		\| NFPA-S =
	\| RPhrases =
	\| SPhrases =
	\| RSPhrases =
	\| FlashPt =		\| FlashPt =
	\| ~~Autoignition~~ =		\| AutoignitionPt =
	\| ExploLimits =		\| ExploLimits =
	\| PEL = }}		\| PEL =
			}}
	}}		}}
	'''Digallic acid''' is a polyphenolic compound found in '']''.<ref>Study of genotoxic, antigenotoxic and antioxidant activities of the digallic acid isolated from Pistacia lentiscus fruits. Wissem Bhouri, Safa Derbel, Ines Skandrani, Jihed Boubaker, Ines Bouhlel, Mohamed B. Sghaier, Soumaya Kilani, Anne M. Mariotte, Marie G. Dijoux-Franca, Kamel Ghedira and Leila Chekir-Ghedir, Toxicology in Vitro, Volume 24, Issue 2, March 2010, pp. 509-515, {{doi\|10.1016/j.tiv.2009.06.024}}</ref> Digallic acid is also present in the molecule of ].<ref>Analysis of gallic, digallic and trigallic acids in tannic acids by high-performance liquid chromatography. P. Delahaye and M. Verzele, Journal of Chromatography A, Volume 265, 1983, pp. 363-367, {{doi\|10.1016/S0021-9673(01)96734-2}}</ref> Digalloyl esters involve either ''-meta'' or ''-para'' ] bonds.<ref></ref>

			'''Digallic acid''' is a polyphenolic compound found in '']''.<ref>{{Cite journal \| last1 = Bhouri \| first1 = W. \| last2 = Derbel \| first2 = S. \| last3 = Skandrani \| first3 = I. \| last4 = Boubaker \| first4 = J. \| last5 = Bouhlel \| first5 = I. \| last6 = Sghaier \| first6 = M. B. \| last7 = Kilani \| first7 = S. \| last8 = Mariotte \| first8 = A. M. \| last9 = Dijoux-Franca \| first9 = M. G. \| last10 = Ghedira \| doi = 10.1016/j.tiv.2009.06.024 \| first10 = K. \| last11 = Chekir-Ghedira \| first11 = L. \| title = Study of genotoxic, antigenotoxic and antioxidant activities of the digallic acid isolated from Pistacia lentiscus fruits \| journal = Toxicology in Vitro \| volume = 24 \| issue = 2 \| pages = 509–515 \| year = 2010 \| pmid = 19563883}}</ref> Digallic acid is also present in the molecule of ].<ref>{{Cite journal \| last1 = Delahaye \| first1 = P. \| last2 = Verzele \| first2 = M. \| doi = 10.1016/S0021-9673(01)96734-2 \| title = Analysis of gallic, digallic and trigallic acids in tannic acids by high-performance liquid chromatography \| journal = Journal of Chromatography A \| volume = 265 \| pages = 363–367 \| year = 1983 }}</ref> Digalloyl esters involve either ''-meta,'' or ''-para'' ] bonds.<ref>{{cite web \| url = http://www.users.miamioh.edu/hagermae/ \| title = The Tannin Handbook \| author = Ann E. Hagerman \| publisher = Miami University }}</ref>
⚫	] is an enzyme that uses digallate to produce ].

		⚫	] is an enzyme that uses digallate to produce ]. This enzyme can also be used to produce digallic acid from ]s.<ref>{{Cite journal
⚫	==References==
			\| last1 = Nierenstein \| first1 = M.
			\| title = A biological synthesis of m-digallic acid
			\| journal = The Biochemical Journal
			\| volume = 26
		⚫	\| issue = 4
			\| pages = 1093–1094
			\| year = 1932
			\| pmid = 16744910
			\| pmc = 1261008
			\| doi=10.1042/bj0261093
			}}</ref>

		⚫	== References ==
	{{Reflist}}		{{Reflist}}

	<!-- ==External links==
	{{commons}} -->

	{{Gallotannin}}		{{Gallotannin}}
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	]		]
	]		]
			]
			]


	{{~~Natural-phenol~~-stub}}		{{aromatic-stub}}

Latest revision as of 20:37, 19 December 2023

Digallic acid
Names

Preferred IUPAC name 3,4-Dihydroxy-5-benzoic acid
Other names Digallate 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate m-digallic acid Digalloyl ester
Identifiers
CAS Number	536-08-3
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL366356
ChemSpider	334
ECHA InfoCard	100.007.842
PubChem CID	341
UNII	404KO0584X
CompTox Dashboard (EPA)	DTXSID50871747
InChI InChI=1S/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)Key: COVFEVWNJUOYRL-UHFFFAOYSA-N InChI=1/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)Key: COVFEVWNJUOYRL-UHFFFAOYAG
SMILES C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O) O=C(O)c2cc(O)c(O)c(OC(=O)c1cc(O)c(O)c(O)c1)c2
Properties
Chemical formula	C₁₄H₁₀O₉
Molar mass	322.225 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Digallic acid is a polyphenolic compound found in Pistacia lentiscus. Digallic acid is also present in the molecule of tannic acid. Digalloyl esters involve either -meta, or -para depside bonds.

Tannase is an enzyme that uses digallate to produce gallic acid. This enzyme can also be used to produce digallic acid from gallotannins.

References

Bhouri, W.; Derbel, S.; Skandrani, I.; Boubaker, J.; Bouhlel, I.; Sghaier, M. B.; Kilani, S.; Mariotte, A. M.; Dijoux-Franca, M. G.; Ghedira, K.; Chekir-Ghedira, L. (2010). "Study of genotoxic, antigenotoxic and antioxidant activities of the digallic acid isolated from Pistacia lentiscus fruits". Toxicology in Vitro. 24 (2): 509–515. doi:10.1016/j.tiv.2009.06.024. PMID 19563883.
Delahaye, P.; Verzele, M. (1983). "Analysis of gallic, digallic and trigallic acids in tannic acids by high-performance liquid chromatography". Journal of Chromatography A. 265: 363–367. doi:10.1016/S0021-9673(01)96734-2.
Ann E. Hagerman. "The Tannin Handbook". Miami University.
Nierenstein, M. (1932). "A biological synthesis of m-digallic acid". The Biochemical Journal. 26 (4): 1093–1094. doi:10.1042/bj0261093. PMC 1261008. PMID 16744910.

Types of gallotannins

Aglycones

Galloylglucoses

Monogalloylglucoses:	1-Galloylglucose Glucogallin
Digalloylglucoses:	1,6-Digalloylglucose 2,6-Digalloylglucose 3,6-Digalloylglucose
Trigalloylglucoses:	1,2,3-Trigalloylglucose 1,2,3-Tri-O-galloyl-β-D-glucose 1,2,6-Trigalloylglucose 1,3,6-Trigalloylglucose
Tetragalloylglucoses:	1,2,3,6-Tetragalloylglucose 1,2,3,6-Tetrakis-O-galloyl-β-D-glucose 1,2,4,6-Tetragalloylglucose 1,2,4,6-Tetrakis-O-galloyl-β-D-glucose
Pentagalloylglucoses:	1,2,3,4,6-Pentagalloylglucose 6-Digalloyl-1,2,3-trigalloylglucose
other	Hexagalloylglucose Heptagalloylglucose Octagalloylglucose Nonagalloylglucose Decagalloylglucose

Galloylquinic acids:

Monogalloylquinic acids:	3-O-Galloylquinic acid Theogallin 4-O-Galloylquinic acid 5-O-Galloylquinic acid
Digalloylquinic acids:	1,4-Di-O-galloylquinic acid 3,4-Di-O-Galloylquinic acid 3,5-Di-O-Galloylquinic acid 4,5-Di-O-Galloylquinic acid
Trigalloylquinic acids:	1,3,4-Tri-O-galloylquinic acid 3,4,5-Tri-O-galloylquinic acid

Galloylshikimic acids:

others

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