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2D Structure
Also known as: 2-hydroxypropanoic acid, Dl-lactic acid, 50-21-5, 2-hydroxypropionic acid, Milk acid, Lactate
Molecular Formula
C3H6O3
Molecular Weight
90.08  g/mol
InChI Key
JVTAAEKCZFNVCJ-UHFFFAOYSA-N
FDA UNII
3B8D35Y7S4

A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed)
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-hydroxypropanoic acid
2.1.2 InChI
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)
2.1.3 InChI Key
JVTAAEKCZFNVCJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C(=O)O)O
2.2 Other Identifiers
2.2.1 UNII
3B8D35Y7S4
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2 Hydroxypropanoic Acid

2. 2 Hydroxypropionic Acid

3. 2-hydroxypropanoic Acid

4. 2-hydroxypropionic Acid

5. Ammonium Lactate

6. D Lactic Acid

7. D-lactic Acid

8. L Lactic Acid

9. L-lactic Acid

10. Lactate

11. Lactate, Ammonium

12. Propanoic Acid, 2-hydroxy-, (2r)-

13. Propanoic Acid, 2-hydroxy-, (2s)-

14. Sarcolactic Acid

2.3.2 Depositor-Supplied Synonyms

1. 2-hydroxypropanoic Acid

2. Dl-lactic Acid

3. 50-21-5

4. 2-hydroxypropionic Acid

5. Milk Acid

6. Lactate

7. Tonsillosan

8. Racemic Lactic Acid

9. Ordinary Lactic Acid

10. Polylactic Acid

11. Ethylidenelactic Acid

12. Lactovagan

13. Acidum Lacticum

14. 26100-51-6

15. Lactic Acid, Dl-

16. Propanoic Acid, 2-hydroxy-

17. Kyselina Mlecna

18. Lacticum Acidum

19. Dl-milchsaeure

20. (+/-)-lactic Acid

21. 598-82-3

22. 1-hydroxyethanecarboxylic Acid

23. Aethylidenmilchsaeure

24. Alpha-hydroxypropionic Acid

25. (rs)-2-hydroxypropionsaeure

26. Fema No. 2611

27. Kyselina 2-hydroxypropanova

28. Propionic Acid, 2-hydroxy-

29. Purac Fcc 80

30. Purac Fcc 88

31. Ccris 2951

32. Hsdb 800

33. (+-)-2-hydroxypropanoic Acid

34. Lurex

35. Lactic Acid, Tech Grade

36. Propanoic Acid, Hydroxy-

37. Sy-83

38. Dl- Lactic Acid

39. Nsc 367919

40. 2-hydroxypropionicacid

41. Ai3-03130

42. Mfcd00004520

43. Hipure 88

44. Nsc-367919

45. .alpha.-hydroxypropanoic Acid

46. .alpha.-hydroxypropionic Acid

47. (r)-2-hydroxy-propionic Acid;h-d-lac-oh

48. Ins No.270

49. E 270

50. (+/-)-2-hydroxypropanoic Acid

51. Chebi:78320

52. Ins-270

53. Poly(l-lactide)

54. 3b8d35y7s4

55. Lactic Acid Usp

56. Ncgc00090972-01

57. Lactic Acid, 1.0n Standardized Solution

58. 2-hydroxy-propionic Acid

59. Lactic Acid (natural)

60. E-270

61. Dsstox_cid_3192

62. Alpha-hydroxypropanoic Acid

63. C01432

64. Dsstox_rid_76915

65. Dsstox_gsid_23192

66. Milchsaure [german]

67. Lactic Acid [jan]

68. Milchsaure

69. Fema Number 2611

70. Kyselina Mlecna [czech]

71. 163894-00-6

72. Cheongin Samrakhan

73. Cas-50-21-5

74. Cheongin Haewoohwan

75. Cheongin Haejanghwan

76. Kyselina 2-hydroxypropanova [czech]

77. Einecs 200-018-0

78. Einecs 209-954-4

79. Lactic Acid [usp:jan]

80. Epa Pesticide Chemical Code 128929

81. Brn 5238667

82. Lactasol

83. 1-hydroxyethane 1-carboxylic Acid

84. Biolac

85. Unii-3b8d35y7s4

86. 2-hydroxy-2-methylacetic Acid

87. Lactide Polymer

88. Chem-cast

89. L- Lactic Acid

90. Dl-polylactic Acid

91. Lactate (tn)

92. Lactic Acid,buffered

93. 4b5w

94. Propanoic Acid, (+-)

95. Dl-lactic Acid, Racemic

96. (.+/-.)-lactic Acid

97. Ec 200-018-0

98. Lactic Acid (7ci,8ci)

99. Lactic Acid (jp17/usp)

100. Lactic Acid, 85%, Fcc

101. Lactic Acid, Racemic, Usp

102. Nciopen2_000884

103. Lactic Acid (+-)

104. Dl-lactic Acid [mi]

105. Lactic Acid, Unspecified Form

106. Lactic Acid [who-ip]

107. (rs)-2-hydroxypropanoic Acid

108. Lactic Acid (fragrance Grade)

109. Lacticum Acidum [hpus]

110. Dl-lactic Acid (90per Cent)

111. Chembl1200559

112. Dtxsid7023192

113. Lactic Acid, Natural, >=85%

114. Bdbm23233

115. L-lactic Acid Or Dl-lactic Acid

116. Lactic Acid, 85 Percent, Fcc

117. Lactic Acid, Dl- [ii]

118. Dl-lactic Acid, ~90% (t)

119. Dl-lactic Acid, Ar, >=88%

120. Dl-lactic Acid, Lr, >=88%

121. Dl- Lactic Acid [who-dd]

122. Lactic Acid, 10 Percent Solution

123. Hy-b2227

124. Propanoic Acid, 2-hydroxy- (9ci)

125. Tox21_111049

126. Tox21_202455

127. Tox21_303616

128. Bbl027466

129. Nsc367919

130. Stl282744

131. Akos000118855

132. Akos017278364

133. Tox21_111049_1

134. Acidum Lacticum [who-ip Latin]

135. Am87208

136. Db04398

137. Sb44647

138. Sb44652

139. Dl-lactic Acid, 85 % (w/w), Syrup

140. Propanoic Acid,2-hydroxy-,(.+/-.)-

141. 2-hydroxypropionic Acid, Dl-lactic Acid

142. Ncgc00090972-02

143. Ncgc00090972-03

144. Ncgc00257515-01

145. Ncgc00260004-01

146. 26811-96-1

147. Lactic Acid, 85 Percent, Reagent, Acs

148. Db-071134

149. Lactic Acid 100 Microg/ml In Acetonitrile

150. Cs-0021601

151. Ft-0624390

152. Ft-0625477

153. Ft-0627927

154. Ft-0696525

155. Ft-0774042

156. L0226

157. Lactic Acid Solution, Acs Reagent, >=85%

158. Lactic Acid Solution, Usp, 88.0-92.0%

159. Lactic Acid Solution, P.a., 84.5-85.5%

160. Lactic Acid, Meets Usp Testing Specifications

161. D00111

162. F71201

163. A877374

164. Dl-lactic Acid, Saj First Grade, 85.0-92.0%

165. Q161249

166. Dl-lactic Acid, Jis Special Grade, 85.0-92.0%

167. Lactic Acid Solution, Vetec(tm) Reagent Grade, 85%

168. F2191-0200

169. Bc10f553-5d5d-4388-bb74-378ed4e24908

170. Lactic Acid, United States Pharmacopeia (usp) Reference Standard

171. Lactic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

172. Dl-lactic Acid 90%, Synthetic, Meets The Analytical Specifications Of Ph. Eur.

173. 152-36-3

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 90.08 g/mol
Molecular Formula C3H6O3
XLogP3-0.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass90.031694049 g/mol
Monoisotopic Mass90.031694049 g/mol
Topological Polar Surface Area57.5 Ų
Heavy Atom Count6
Formal Charge0
Complexity59.1
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Lactic acid is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of March 17, 2016: https://clinicaltrials.gov/ct2/results?term=lactic+acid&Search=Search


(VET): Has been used as a caustic, and in dilute solutions to irrigate tissues; as an intestinal antiseptic and antiferment.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 990


A 10% solution is used as a bactericidal agent on the skin of neonates. ... A 16.7% solution in flexible collodion is used to remove warts and small cutaneous tumors.

Troy, D.B. (Ed); Remmington The Science and Practice of Pharmacy. 21 st Edition. Lippincott Williams & Williams, Philadelphia, PA 2005, p. 1087


Acidulant

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 990


4.2 Drug Indication

For use as an alkalinizing agent.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Lactic acid produces a metabolic alkalinizing effect.


5.2 ATC Code

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AD - Organic acids

G01AD01 - Lactic acid


5.3 Absorption, Distribution and Excretion

L-lactic acid occurs in small quantities in the blood and muscle fluid of humans and animals; the concentration of lactic acid in these fluids increases after vigorous activity. L-lactic acid is also present in the liver, kidneys, thymus gland, human amniotic fluid, and other organs and body fluids.

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology, 17 (Suppl.1): 1-203 (1998)


A primed infusion study was performed /in humans/ using radioactive L-lactic acid. The virtual volume of distribution of lactate was 49.4% of body weight. The lactate pool size and turnover time were estimated as 0.029 g/kg and 18.4 min, respectively.

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology, 17 (Suppl.1): 1-203 (1998)


In the body, lactate is distributed equivalently to, or slightly less than, total body water. It diffuses readily across cell membranes, primarily by passive transport; under certain conditions, the distribution could be uneven or the lactate pool could consist of several smaller pools with differing rate constants.

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology, 17 (Suppl.1): 1-203 (1998)


The percutaneous absorption of topically applied 5% [14C]-lactic acid in an oil-in-water cream was measured using rats. After 3 days, 50% of the applied lactic acid had penetrated the skin.

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology, 17 (Suppl.1): 1-203 (1998)


For more Absorption, Distribution and Excretion (Complete) data for LACTIC ACID (6 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

... Propylene glycol ... is oxidized to lactic acid or pyruvic acid by two pathways. These two metabolites are then used by the body as sources of energy either by oxidation through the tricarboxylic acid cycle or by generation of glycogen through the glycolytic pathway.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 31


Lactic acid diffuses through muscle tissue and is transported to the liver in the bloodstream. In the liver, it is converted to glucose by gluconeogenesis. Lactic acid can also be further catabolized in the lactic acid cycle (also known as the Cori cycle).

Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additives Ser 48: Lactic acid (2002). Available from, as of April 19, 2006: https://www.inchem.org/documents/jecfa/jecmono/v48je16.htm


L-lactic acid is a normal metabolic intermediate produced by most mammalian cells and other organisms, such as bacteria; it is metabolized in preference to D-lactic acid in man, dogs, and rats. Lactic acid is converted to pyruvic acid by lactic acid dehydrogenase.

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology, 17 (Suppl.1): 1-203 (1998)


In animals, lactate that is generated by anaerobic metabolism can be transported to other more aerobic tissues, such as the liver, where it can be reconverted to pyruvate. The pyruvate can then be further metabolized, reconverted to carbohydrate material as free glucose, or stored as glycogen.

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology, 17 (Suppl.1): 1-203 (1998)


For more Metabolism/Metabolites (Complete) data for LACTIC ACID (8 total), please visit the HSDB record page.


5.5 Mechanism of Action

Lactate ions are metabolized ultimately to carbon dioxide and water, which requires the consumption of hydrogen cations.