<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:44 UTC</creation_date>
  <update_date>2025-11-18 22:50:08 UTC</update_date>
  <accession>FDB003292</accession>
  <name>Lactic acid</name>
  <description>Widely distributed in nature as a fermentation product from starch, molasses, potatoes etc. "Natural" lactic acid is produced commercially by fermentation of beet/cane sugar or glucose. No commercial lactic acid is dairy-based. Synthetic lactic acid is a racemic mixture of the L- and D-forms. Among the oldest known preservatives used to preserve milk products and a broad range of traditional fermented vegetables. The modern use of lactic acid as a food additive covers several functions: flavouring, acidity control, preservation. Due to its mild flavour, lactic acid can be used in high concentrationsand is also in brewing, manuf. of cheese and confectionery

Lactic acid is chiral and has two optical isomers. One is known as L-(+)-lactic acid or (S)-lactic acid and the other, its mirror image, is D-(-)-lactic acid or (R)-lactic acid. L-(+)-Lactic acid is the biologically important isomer. Lactic acid is found in many foods, some of which are sunflower, apple, common grape, and borage.</description>
  <synonyms>
    <synonym>(+-)-2-Hydroxypropanoic acid</synonym>
    <synonym>(+/-)-Lactic acid</synonym>
    <synonym>&amp;alpha;-Hydroxypropanoic acid</synonym>
    <synonym>&amp;alpha;-Hydroxypropionic acid</synonym>
    <synonym>1-Hydroxyethane 1-carboxylic acid</synonym>
    <synonym>1-Hydroxyethanecarboxylic acid</synonym>
    <synonym>2-Hydroxy-2-methylacetic acid</synonym>
    <synonym>2-Hydroxypropionic acid</synonym>
    <synonym>alpha-Hydroxypropanoic acid</synonym>
    <synonym>alpha-Hydroxypropionic acid</synonym>
    <synonym>Chem-Cast</synonym>
    <synonym>DL-Lactic acid</synonym>
    <synonym>E270</synonym>
    <synonym>Enyper</synonym>
    <synonym>FEMA 2611</synonym>
    <synonym>Kerlactine</synonym>
    <synonym>Lactasol</synonym>
    <synonym>Lactate</synonym>
    <synonym>Lactic acid, 8CI, JAN, USAN</synonym>
    <synonym>Lactogyn</synonym>
    <synonym>Lactolavol</synonym>
    <synonym>Lactovagan</synonym>
    <synonym>Propanoic acid, 2-hydroxy- (9CI)</synonym>
    <synonym>Propionic acid, 2-hydroxy-</synonym>
    <synonym>Tonsillosan</synonym>
    <synonym>Variclene</synonym>
  </synonyms>
  <chemical_formula>C3H6O3</chemical_formula>
  <average_molecular_weight>90.0779</average_molecular_weight>
  <monisotopic_moleculate_weight>90.031694058</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxypropanoic acid</iupac_name>
  <traditional_iupac>lactic acid</traditional_iupac>
  <cas_registry_number>50-21-5</cas_registry_number>
  <smiles>CC(O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)</inchi>
  <inchikey>JVTAAEKCZFNVCJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.</description>
    <direct_parent>Alpha hydroxy acids and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Alpha hydroxy acids and derivatives</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>2-hydroxy monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>liquid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.62e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>16.8 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.47</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>3.78</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-hydroxypropanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>90.0779</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>90.031694058</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C3H6O3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>JVTAAEKCZFNVCJ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>57.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>18.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>8.05</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>57373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>61227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>135865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>143599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22091</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>28358</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Apple</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Malus pumila</name_scientific>
      <ncbi_taxonomy_id>283210</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beer</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>137.5</average_value>
      <max_value>275.0</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Black elderberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sambucus nigra</name_scientific>
      <ncbi_taxonomy_id>4202</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Borage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Borago officinalis</name_scientific>
      <ncbi_taxonomy_id>13363</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cocoa bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Theobroma cacao</name_scientific>
      <ncbi_taxonomy_id>3641</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common grape</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vitis vinifera</name_scientific>
      <ncbi_taxonomy_id>29760</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cottonseed</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gossypium</name_scientific>
      <ncbi_taxonomy_id>3633</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden rhubarb</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rheum rhabarbarum</name_scientific>
      <ncbi_taxonomy_id>3621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden tomato (var.)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum lycopersicum var. lycopersicum</name_scientific>
      <ncbi_taxonomy_id>397755</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ginkgo nuts</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ginkgo biloba</name_scientific>
      <ncbi_taxonomy_id>3311</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guava</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Psidium guajava</name_scientific>
      <ncbi_taxonomy_id>120290</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Lettuce</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lactuca sativa</name_scientific>
      <ncbi_taxonomy_id>4236</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Opium poppy</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Papaver somniferum</name_scientific>
      <ncbi_taxonomy_id>3469</ncbi_taxonomy_id>
      <average_value>1500.0</average_value>
      <max_value>1500.0</max_value>
      <min_value>1500.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Potato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum tuberosum</name_scientific>
      <ncbi_taxonomy_id>4113</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Red raspberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rubus idaeus</name_scientific>
      <ncbi_taxonomy_id>32247</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sour cherry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus cerasus</name_scientific>
      <ncbi_taxonomy_id>140311</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sunflower</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Helianthus annuus</name_scientific>
      <ncbi_taxonomy_id>4232</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Tamarind</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Tamarindus indica</name_scientific>
      <ncbi_taxonomy_id>58860</ncbi_taxonomy_id>
    </food>
    <food>
      <name>White wine</name>
      <food_type>Type 2</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>100.1</average_value>
      <max_value>200.0</max_value>
      <min_value>0.2</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>odorless</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Acidulant</name>
      <id>23</id>
      <definition>Any substance which is added to food to preserve or enhance its flavour and/or appearance.</definition>
    </health_effect>
    <health_effect>
      <name>Anti leukorrheic</name>
      <id>398</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti xerotic</name>
      <id>696</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-oxidant</name>
      <id>502</id>
      <definition>A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-vaginitic</name>
      <id>686</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Irritant</name>
      <id>1055</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Keratolytic</name>
      <id>1060</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Name</name>
      <id>936</id>
      <definition>A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.</definition>
    </health_effect>
  </health_effects>
</compound>
