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Hydroxycarboxylic acid

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Hydroxycarboxylic acids are carboxylic acids containing one or more hydroxy (alcohol) functional groups. They are of particular interest because several are bioactive and some are useful precursors to polyesters. The inventory is large. Important or common examplesGlycolic acid, HOCH2CO2H, the parent hydroxycarboxylic acid, precursor to lacquersHydroxypropionic acids, e.g., CH3CH(OH)CO2H (lactic acid), component of milk.

SerineSerineNames IUPAC nameSerineSystematic IUPAC name2-Amino-3-hydroxypropanoic acidIdentifiers CAS NumberL: 56-45-1D/L: 302-84-1D: 312-84-53D model (JSmol)L: Interactive imageD/L Zwitterion: Interactive imageChEBIL: CHEBI:17115ChEMBLL: ChEMBL11298ChemSpiderL: 5736D/L: 597D: 64231DrugBankL: DB00133ECHA InfoCard100.000.250EC NumberL: 206-130-6IUPHAR/BPSL: 726KEGGL: C00065D: C00740PubChemCIDL: 5951D/L: 617D: 71077UNIIL: 452VLY9402D/L: 00PAR1C66FD: 1K77H2Z9B1CompTox Dashboard(EPA)L: DTXSID60883230InChIInChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1Key: MTCFGRXMJLQNBG-REOHCLBHSA-ND/L: Key: MTCFGRXMJLQNBG-UHFFFAOYSA-ND: Key: MTCFGRXMJLQNBG-UWTATZPHSA-NSMILESL: C([C@@H](C(=O)O)N)OD/L Zwitterion: C([C@@H](C(=O)[O-])[NH3+])OProperties Chemical formulaC3H7NO3Molar mass105.093 g·mol Appearance white crystals or powder Density1.603 g/cm (22 °C) Melting point246 °C (475 °F; 519 K) decomposes Solubility in watersoluble Acidity (pKa) 2.21 (carboxyl), 9.15 (amino) Supplementary data page Serine (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Serine (symbol Ser or S) is an α-amino acid that is used in the biosynthesis of proteins.TyrosineTyrosineNames IUPAC nameTyrosineSystematic IUPAC name2-Amino-3-(4-hydroxyphenyl)propanoic acidIdentifiers CAS Number60-18-4 (L)3D model (JSmol)Interactive imageZwitterion: Interactive imageChEBICHEBI:17895ChEMBLChEMBL925ChemSpider5833DrugBankDB00135ECHA InfoCard100.000.419IUPHAR/BPS4791KEGGC00082PubChemCID6057UNII42HK56048UCompTox Dashboard(EPA)DTXSID1023730InChIInChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1Key: OUYCCCASQSFEME-QMMMGPOBSA-NKey: OUYCCCASQSFEME-UHFFFAOYSA-NKey: OUYCCCASQSFEME-MRVPVSSYSA-NSMILESN[C@@H](Cc1ccc(O)cc1)C(O)=OZwitterion: [NH3+][C@@H](Cc1ccc(O)cc1)C([O-])=OProperties Chemical formulaC9H11NO3Molar mass181.191 g·mol Appearance white solid Solubility in water45.3 mg/100 mL Magnetic susceptibility (χ)−105.3·10 cm/mol Hazards NFPA 704 (fire diamond) 110Supplementary data page Tyrosine (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).L-Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins.Gluconic acidGluconic acidGluconic acid is an organic compound with molecular formula C6H12O7 and condensed structural formula HOCH2(CHOH)4CO2H. A white solid, it forms the gluconate anion in neutral aqueous solution. The salts of gluconic acid are known as "gluconates". Gluconic acid, gluconate salts, and gluconate esters occur widely in nature because such species arise from the oxidation of glucose. Some drugs are injected in the form of gluconates.Hydroxy groupHydroxy groupIn chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula−OH and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anionHO, called hydroxide, and the neutral radicalHO·, known as the hydroxyl radical, consist of an unbonded hydroxy group.GlucoseGlucoseGlucose is a sugar with the molecular formulaC6H12O6. It is the most abundant monosaccharide, a subcategory of carbohydrates. It is made from water and carbon dioxide during photosynthesis by plants and most algae. It is used by plants to make cellulose, the most abundant carbohydrate in the world, for use in cell walls, and by all living organisms to make adenosine triphosphate (ATP), which is used by the cell as energy. Glucose is often abbreviated as Glc.Functional groupFunctional groupIn organic chemistry, a functional group is any substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis.Lactic acidLactic acidNames Preferred IUPAC name2-hydroxypropanoic acidOther names lactic acidmilk acidIdentifiers CAS Number50-21-579-33-4 (L)10326-41-7 (D)3D model (JSmol)Interactive imageBeilstein Reference1720251 ChEBICHEBI:422ChEMBLChEMBL330546ChemSpider96860ECHA InfoCard100.000.017EC Number200-018-0E numberE270 (preservatives)Gmelin Reference362717 IUPHAR/BPS2932KEGGD00111C00186C00256PubChemCID612RTECS numberOD2800000UNII3B8D35Y7S4F9S9FFU82N (L)3Q6M5SET7W (D)UN number3265 CompTox Dashboard(EPA)DTXSID7023192InChIInChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1Key: JVTAAEKCZFNVCJ-REOHCLBHSA-NSMILESCC(O)C(=O)OProperties Chemical formulaC3H6O3Molar mass90.078 g·mol Melting point18 °C (64 °F; 291 K) Boiling point122 °C (252 °F; 395 K) at 15mmHg Solubility in water86.1% w/w at 20°C 88.6% w/w at 25°C Acidity (pKa) 3.86, 15.1 Thermochemistry Std enthalpy ofcombustion(ΔcH298)1361.9kJ/mol, 325.5kcal/mol, 15.1kJ/g, 3.61kcal/g Related compounds Other anionslactate Related carboxylic acidsacetic acidglycolic acidpropionic acid3-hydroxypropanoic acidmalonic acidbutyric acidhydroxybutyric acidRelated compounds1-propanol2-propanolpropionaldehydeacroleinsodium lactateethyl lactatePharmacology ATC codeG01AD01 (WHO) QP53AG02 (WHO) Hazards GHS labelling: PictogramsHazard statementsH315, H318Precautionary statementsP280, P305+P351+P338Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Yverify ( ?)Hydroxypropionic acidHydroxypropionic acid, or alternately hydroxypropanoic acid, may refer to either of two isomeric chemical compounds: 2-Hydroxypropionic acid (lactic acid) 3-Hydroxypropionic acid (hydracrylic acid) The carboxylate is known as hydroxypropionate or hydroxypropanoate.Glycolic acidGlycolic acidNames Preferred IUPAC nameHydroxyacetic acidOther names Hydroacetic acid2-Hydroxyethanoic acidIdentifiers CAS Number79-14-13D model (JSmol)Interactive imageChEBICHEBI:17497ChEMBLChEMBL252557ChemSpider737DrugBankDB03085ECHA InfoCard100.001.073EC Number201-180-5KEGGC00160PubChemCID757RTECS numberMC5250000UNII0WT12SX38SCompTox Dashboard(EPA)DTXSID0025363InChIInChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)Key: AEMRFAOFKBGASW-UHFFFAOYSA-NInChI=1/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)Key: AEMRFAOFKBGASW-UHFFFAOYARSMILESOC(=O)COProperties Chemical formulaC2H4O3Molar mass76.051 g·mol Appearance White powder or colorless crystals Density1.49 g/cm Melting point75 °C (167 °F; 348 K) Boiling point100 °C (212 °F; 373 K) Decomposes above 100 °C Solubility in water70% solution Solubility in other solvents Alcohols, acetone,acetic acid andethyl acetatelog P−1.05 Vapor pressure1.051 kPa (80 °C) Acidity (pKa) 3.83 Hazards Occupational safety and health (OHS/OSH): Main hazardsCorrosive GHS labelling: PictogramsSignal wordDangerHazard statementsH302, H314, H332Precautionary statementsP260, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P405, P501NFPA 704 (fire diamond) 311Flash point300 °C (572 °F; 573 K) Lethal dose or concentration (LD, LC): LD50 (median dose)1950 mg/kg (rat, oral)2040 mg/kg (rat, oral) LC50 (median concentration)7.7 ppm (rat, 4h)3.6 ppm (rat, 4h) Related compounds Related α-hydroxy acidsLactic acidRelated compoundsGlycolaldehydeAcetic acidGlycerolExcept where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Nverify ( ?)Alcohol (chemistry)Alcohol (chemistry)In chemistry, an alcohol (from Arabic al-kuḥl'the kohl') is a type of organic compound that carries at least one hydroxyl (−OH) functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugar alcohols and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-attracted) properties.Carboxylic acidCarboxylic acidIn organic chemistry, a carboxylic acid is a polar, organic acid that contains a carboxyl group (−C(=O)−OH) attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH, with R referring to an organyl group (e.g., alkyl, alkenyl, aryl), or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids.PolyesterPolyesterPolyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include some natural products, such as those found in plants and insects. Natural polyesters and a few synthetic ones are biodegradable, but most commercial polyesters are not. Polyesters are used extensively in clothing.

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