Anthranilic acid

Anthranilic acid

Chembox new
ImageFile = Anthranilic acid 2.svg
ImageName = Anthranilic Acid
IUPACName = 2-aminobenzoic acid
OtherNames = vitamin L1, Anthranilate
Section1 = Chembox Identifiers
CASNo = 118-92-3
ChemSpiderID = 222
Section2 = Chembox Properties
C=7|H=7|N=1|O=2
Solubility = 5.7 g/L (25 ºC)
Solvent =
SolubleOther = Hot water
Density = 1.4 g/cm3
MeltingPt = 146-148 °C
BoilingPt = Sublimes [ [http://www.inchem.org/documents/icsc/icsc/eics1295.htm IPCS] ]
Section7 = Chembox Hazards
ExternalMSDS = [http://newsearchus.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?action=PowerSearch&query=msds._msdsID%3D749&sort=&target=msds&from=0&realQuery=rn.value%3D%3D%22118-92-3%22&searchTemplate=rn.value%3D%3D%3F&searchValue=118-92-3&history=off&options=brandqtyoffer&format=ccd External (html)]
EUClass =
RPhrases = R36 R37
SPhrases = S26 S39
FlashPt = >150 °C

Anthranilic acid is the organic compound with the formula C6H4(NH2)CO2H. This amino acid is white solid when pure, although commercial samples may appear yellow. The molecule consists of a benzene ring with two adjacent functional groups, a carboxylic acid and an amine. Because these two groups are polar, this organic compound is highly soluble in water. It is sometimes referred to as vitamin L.

Biological role

Anthranilic acid is biosynthesized from chorismic acid. It is the precursor to the amino acid tryptophan via the attachment of phosphoribosyl pyrophosphate to the amine group.

Uses

Anthranilic acid is used as an intermediate for production of dyes, pigments, and saccharin. It and its esters are used in preparing perfumes to imitate jasmine and orange, pharmaceuticals ( loop diuretics eg. furosemide) and UV-absorber as well as corrosion inhibitors for metals and mold inhibitors in soya sauce.

Anthranilic acid can be used in organic synthesis to generate the benzyne intermediate. [OrgSynth | author = Logullo, F. M.; Seitz, A. H.; Friedman, L. | title = Benzenediazonium-2-carboxy- and Biphenylene | collvol = 5 | collvolpages = 54 | year = 1973 | prep = cv5p0054]

ee also

* Kynureninase

References


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Look at other dictionaries:

  • anthranilic acid — [an΄thrə nil′ik] n. [ ANTHR(ACENE) + ANIL(INE) + IC] a yellow crystalline compound, NH2C6H4COOH, used in the manufacture of dyes, drugs, etc …   English World dictionary

  • anthranilic acid — antranilo rūgštis statusas T sritis chemija formulė C₆H₄(NH₂)COOH atitikmenys: angl. anthranilic acid rus. антраниловая кислота ryšiai: sinonimas – 2 aminobenzenkarboksirūgštis …   Chemijos terminų aiškinamasis žodynas

  • anthranilic acid — One of the products of tryptophan catabolism. SYN: o aminobenzoic acid. * * * an·thra·nil·ic acid .an(t) thrə .nil ik n the ortho substituted aminobenzoic acid NH2C6H4COOH used as an intermediate in the manufacture of dyes (as indigo),… …   Medical dictionary

  • anthranilic acid — noun The aromatic amino acid 2 aminobenzoic acid that has biological activity, and is used in organic synthesis …   Wiktionary

  • anthranilic acid — |an(t)thrə|nilik noun Etymology: International Scientific Vocabulary anthr + anilic : a white to pale yellow crystalline acid NH2C6H4COOH originally obtained by fusing indigo with alkali, now made chiefly from phthalimide, and used as an… …   Useful english dictionary

  • anthranilic acid — noun Etymology: International Scientific Vocabulary anthracene + aniline Date: 1845 a crystalline acid NH2C6H4COOH used as an intermediate in the manufacture of dyes (as indigo), pharmaceuticals, and perfumes …   New Collegiate Dictionary

  • anthranilic acid — /an threuh nil ik, an /, Chem. a yellowish crystalline compound, C7H7NO2, soluble in hot water, alcohol, and ether: used in the manufacture of dyes, pharmaceuticals, and perfumes. [ANTHR(ACENE) + ANIL(INE) + IC] * * * …   Universalium

  • N-(p-amylcinnamoyl)anthranilic acid — (ACA) is a modulator of various ion channels in the heart. N (p amylcinnamoyl)anthranilic acid is an effective reversible inhibitor of calcium activated chloride channels and, to a lesser extent, cAMP activated chloride channels, without… …   Wikipedia

  • anthranilic — adjective Of or pertaining to anthranilic acid or its derivatives …   Wiktionary

  • N-Acetylanthranilic acid — IUPAC name 2 acetamidobenzoic acid …   Wikipedia

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