ENSIKLOPEDIA

Tekan Enter untuk memulai pencarian cepat.

Kembali ke Ensiklopedia Arsip Wikipedia Indonesia

Vanillic acid

Vanillic acid^[1]

Names

Preferred IUPAC name

4-Hydroxy-3-methoxybenzoic acid

Other names

4-Hydroxy-m-anisic acid, Vanillate

Identifiers

CAS Number

121-34-6^Y

3D model (JSmol)

Interactive image

ChEBI

CHEBI:30816^Y

ChEMBL

ChEMBL120568^Y

ChemSpider

8155^Y

ECHA InfoCard

100.004.061

KEGG

C06672^Y

PubChem CID

8468

UNII

GM8Q3JM2Y8^Y

CompTox Dashboard (EPA)

DTXSID6059522

InChI

InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)^Y
Key: WKOLLVMJNQIZCI-UHFFFAOYSA-N^Y
InChI=1/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
Key: WKOLLVMJNQIZCI-UHFFFAOYAH

SMILES

COc1cc(ccc1O)C(=O)O

Properties

Chemical formula

C₈H₈O₄

Molar mass

168.148 g·mol⁻¹

Appearance

White to light yellow powder or crystals

Melting point

210 to 213 °C (410 to 415 °F; 483 to 486 K)

Hazards

NFPA 704 (fire diamond)

Related compounds

Vanillin, vanillyl alcohol

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 ?)

Infobox references

Chemical compound

Vanillic acid (4-hydroxy-3-methoxybenzoic acid) is a dihydroxybenzoic acid derivative used as a flavoring agent. It is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid.^[2]^[3]

Occurrence in nature

The highest amount of vanillic acid in plants known so far is found in the root of Angelica sinensis,^[4] an herb indigenous to China, which is used in traditional Chinese medicine.

Occurrences in food

Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), is rich in vanillic acid (1616±94 mg/kg).^[5] It is one of the main natural phenols in argan oil.^{[citation needed]} It is also found in wine and vinegar.^[6]

Metabolism

Vanillic acid is one of the main catechins metabolites found in humans after consumption of green tea infusions.^[7]

Synthesis

Vanillic acid can be obtained from the oxidation of vanillin by various oxidizing agents.

References

↑ "Vanillic acid (4-hydroxy-3-methoxybenzoic acid)". chemicalland21.com. Archived from the original on 2009-01-29. Retrieved 2009-01-28.
↑ Lesage-Meessen L, Delattre M, Haon M, Thibault JF, Ceccaldi BC, Brunerie P, Asther M (October 1996). "A two-step bioconversion process for vanillin production from ferulic acid combining Aspergillus niger and Pycnoporus cinnabarinus". J. Biotechnol. 50 (2–3): 107–113. doi:10.1016/0168-1656(96)01552-0. PMID 8987621.
↑ Civolani C, Barghini P, Roncetti AR, Ruzzi M, Schiesser A (June 2000). "Bioconversion of ferulic acid into vanillic acid by means of a vanillate-negative mutant of Pseudomonas fluorescens strain BF13". Appl. Environ. Microbiol. 66 (6): 2311–2317. Bibcode:2000ApEnM..66.2311C. doi:10.1128/AEM.66.6.2311-2317.2000. PMC 110519. PMID 10831404.
↑ Duke, JA (1992). Handbook of phytochemical constituents of GRAS herbs and other economic plants. CRC Press, 999 edition. ISBN 978-0-8493-3865-6. Archived from the original on 2015-09-23. Retrieved 2012-01-07.
↑ Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST (Jun 2008). "Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Açaí (Euterpe oleracea Mart.)". J Agric Food Chem. 56 (12): 4631–4636. doi:10.1021/jf800161u. PMID 18522407.
↑ Gálvez MC, Barroso CG, Pérez-Bustamante JA (1994). "Analysis of polyphenolic compounds of different vinegar samples". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 199: 29–31. doi:10.1007/BF01192948. S2CID 91784893.
↑ Pietta PG, Simonetti P, Gardana C, Brusamolino A, Morazzoni P, Bombardelli E (1998). "Catechin metabolites after intake of green tea infusions". BioFactors. 8 (1–2): 111–8. doi:10.1002/biof.5520080119. PMID 9699018. S2CID 37684286.

Types of gallotannins

Aglycones

Digallic acid
Gallic acid

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:

4-O-Galloylshikimic acid
5-O-Galloylshikimic acid
3,5-Di-O-galloylshikimic acid
3,4,5-Tri-O-galloylshikimic acid

others

1,2,6-Trigalloylalloside
1,3,6-Trigalloylalloside
1,2,3,6-Tetragalloylalloside
1-O-Galloylquercitol
1,4-Di-O-galloylquercitol

Sumber data: id.wikipedia.org via REST API v1