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2D Structure
Also known as: 501-30-4, 5-hydroxy-2-(hydroxymethyl)-4h-pyran-4-one, 5-hydroxy-2-(hydroxymethyl)-4-pyrone, 5-hydroxy-2-(hydroxymethyl)pyran-4-one, 5-hydroxy-2-hydroxymethyl-4-pyrone, 4h-pyran-4-one, 5-hydroxy-2-(hydroxymethyl)-
Molecular Formula
C6H6O4
Molecular Weight
142.11  g/mol
InChI Key
BEJNERDRQOWKJM-UHFFFAOYSA-N
FDA UNII
6K23F1TT52

kojic acid is a natural product found in Marrubium cylleneum, Aspergillus terricola, and other organisms with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-hydroxy-2-(hydroxymethyl)pyran-4-one
2.1.2 InChI
InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2
2.1.3 InChI Key
BEJNERDRQOWKJM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=C(OC=C(C1=O)O)CO
2.2 Other Identifiers
2.2.1 UNII
6K23F1TT52
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5-((3-aminopropyl)phosphinooxy)-2-(hydroxymethyl)-4h-pyran-4-one

2. Kojyl-appa

2.3.2 Depositor-Supplied Synonyms

1. 501-30-4

2. 5-hydroxy-2-(hydroxymethyl)-4h-pyran-4-one

3. 5-hydroxy-2-(hydroxymethyl)-4-pyrone

4. 5-hydroxy-2-(hydroxymethyl)pyran-4-one

5. 5-hydroxy-2-hydroxymethyl-4-pyrone

6. 4h-pyran-4-one, 5-hydroxy-2-(hydroxymethyl)-

7. Acido Kojico

8. 2-hydroxymethyl-5-hydroxy-gamma-pyrone

9. 2-(hydroxymethyl)-5-hydroxy-4h-pyran-4-one

10. Mfcd00006580

11. 5-hydroxy-2-hydroxymethyl-4h-4-pyranone

12. 5-hydroxy-2-hydroxymethyl-pyran-4-one

13. 5-hydroxy-2-hydroxymethyl-4h-pyran-4-one

14. Pyran-4-one, 5-hydroxy-2-(hydroxymethyl)

15. Chembl287556

16. 123712-78-7

17. Chebi:43572

18. Nsc1942

19. 6k23f1tt52

20. Nsc-1942

21. Ncgc00017325-03

22. Ncgc00017325-06

23. Dsstox_cid_20236

24. Dsstox_rid_79455

25. Dsstox_gsid_40236

26. Cas-501-30-4

27. Ccris 4131

28. Nsc 1942

29. Einecs 207-922-4

30. Brn 0120895

31. Kojisaeure

32. Unii-6k23f1tt52

33. Ai3-02549

34. Hsdb 7664

35. Kojic Acid Solution

36. Spectrum_000191

37. Kojic Acid [mi]

38. Spectrum2_001828

39. Spectrum3_001704

40. Spectrum4_000571

41. Spectrum5_001085

42. Natural Kojic Acid Powder

43. Kojic Acid [hsdb]

44. Kojic Acid [iarc]

45. Kojic Acid [inci]

46. Kojic Acid Dipalmitate 5kg

47. Kojic Acid [mart.]

48. Oprea1_038773

49. Schembl36895

50. Bspbio_003288

51. Kbiogr_001002

52. Kbioss_000671

53. Kojic Acid [who-dd]

54. 5-18-02-00516 (beilstein Handbook Reference)

55. Bidd:er0501

56. Divk1c_000923

57. Spbio_001875

58. Kojic Acid, Analytical Standard

59. Megxm0_000388

60. Wln: T6o Dvj B1q Eq

61. Dtxsid2040236

62. Acon1_000622

63. Bejnerdrqowkjm-uhfffaoysa-

64. Hms502o05

65. Kbio1_000923

66. Kbio2_000671

67. Kbio2_003239

68. Kbio2_005807

69. Kbio3_002508

70. Ninds_000923

71. Hms3604l04

72. Kuc106760n

73. Tnp00261

74. 2-hydroxymethyl-5-hydroxy-?-pyrone

75. 2-hydroxymethyl-5-hydroxy-g-pyrone

76. Tox21_110814

77. Tox21_113449

78. Bbl010645

79. Bdbm50031467

80. Ccg-38458

81. S5174

82. Stk801688

83. Zinc13831818

84. Akos000120649

85. Tox21_110814_1

86. 5-hydroxy-2-hydroxymethyl-i(3)-pyron

87. Db01759

88. Hy-w050154

89. Idi1_000923

90. Smp1_000171

91. Ncgc00017325-01

92. Ncgc00017325-02

93. Ncgc00017325-04

94. Ncgc00017325-05

95. Ncgc00017325-10

96. Ncgc00142361-01

97. Ncgc00168903-01

98. Ncgc00168903-02

99. Ncgc00181145-01

100. Ac-11658

101. As-11648

102. Kojic Acid, Purum, >=98.0% (hplc)

103. Ksc-11-228-2

104. Sy018009

105. 2-hydroxymethyl-5-hydroxy-4-pyrone

106. 2-hydroxymethyl-5-hydroxy-4h-pyran-4-one

107. Cs-0032701

108. Ft-0627581

109. K0010

110. K0012

111. 01k304

112. C91105

113. K-7000

114. 2-hydroxymethyl-5-hydroxy-.gamma.-pyrone

115. Q416285

116. Sr-01000945134

117. Sr-01000945134-1

118. 5-hydroxy-2-(hydroxymethyl)-4h-pyran-4-one Solution

119. C65a72e0-0e46-4af4-aa68-178eca2e5fcc

120. F0001-1307

121. Z381040328

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 142.11 g/mol
Molecular Formula C6H6O4
XLogP3-0.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass142.02660867 g/mol
Monoisotopic Mass142.02660867 g/mol
Topological Polar Surface Area66.8 Ų
Heavy Atom Count10
Formal Charge0
Complexity214
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Depigmenting agent /for skin lightening/

PMID:18369335 Zhu W, Gao J; J Investig Dermatol Symp Proc 13 (1): 20-4 (2008)


Melasma is a chronic and recurrent disorder. It has been underdiagnosed and undertreated due to lack of effective therapies and the perception that it is merely a cosmetic nuisance. Hydroquinone, corticosteroids, licorice extracts and kojic acid have been used as monotherapy to treat melasma. However, the present standard of care in melasma therapy is combination therapy. To date, the most effective treatment is a triple-combination agent that contains hydroquinone 4%, tretinoin 0.05% and fluocinolone acetonide 0.01%...

Rendon MI; J Drugs Dermatol (5 Suppl):S27-34 (2004)


... Combination regimens, including frequent applications of superficial- and medium-depth chemical peels, appear to be particularly effective and well tolerated in dark-skinned patients with melanosis. Post-inflammatory hyperpigmentation is the result of excess pigment deposition following an inflammatory skin disorder. Topical tretinoin, hydroquinone, azelaic acid, kojic acid, and glycolic acid peels have been employed with variable degrees of success...

PMID:15186195 Stratigos AJ, Katsambas A; Am J Clin Dermatol 5 (3): 161-8 (2004)


Facial and neck pigmentations are ... common in middle-aged women, and are related to endogenous (hormones) and exogenous factors (such as use of cosmetics and perfumes, and exposure to sun radiation). Melasma (chloasma) is the most common cause of facial pigmentation, but there are many other forms such as Riehl's melanosis, poikiloderma of Civatte, erythrose peribuccale pigmentaire of Brocq, erythromelanosis follicularis of the face and neck, linea fusca, and cosmetic hyperpigmentations. Treatment of melasma and other facial pigmentations has always been challenging and discouraging.... Several hypopigmenting agents have been used with differing results. Topical hydroquinone 2 to 4% alone or in combination with tretinoin 0.05 to 0.1% is an established treatment. Topical azelaic acid 15 to 20% can be as efficacious as hydroquinone, but is less of an irritant. Tretinoin is especially useful in treating hyperpigmentation of photoaged skin. Kojic acid, alone or in combination with glycolic acid or hydroquinone, has shown good results, due to its inhibitory action on tyrosinase. Chemical peels are useful to treat melasma: trichloroacetic acid, Jessner's solution, Unna's paste, alpha-hydroxy acid preparations, kojic acid, and salicyclic acid, alone or in various combinations have shown good results. In contrast, laser therapies have not produced completely satisfactory results, because they can induce hyperpigmentation and recurrences can occur. New laser approaches could be successful at clearing facial hyperpigmentation in the future.

PMID:11702317 Perez-Bernal A et al; Am J Clin Dermatol 1 (5): 261-8 (2000)


For more Therapeutic Uses (Complete) data for KOJIC ACID (7 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)


5.2 Metabolism/Metabolites

The structure of kojic acid indicates a relatively simple route of metabolism much like dietary hexoses.

PMID:11259181 Burdock GA et al; Regul Toxicol Pharmacol 33 (1): 80-101 (2001)


5.3 Mechanism of Action

The mechanism of action of kojic acid is well defined and it has been shown to act as a competitive and reversible inhibitor of animal and plant polyphenol oxidases, xanthine oxidase, and D- and some L-amino acid oxidases.

PMID:11259181 Burdock GA et al; Regul Toxicol Pharmacol 33 (1): 80-101 (2001)


The activation of NF-kappaB induced by kojic acid, an inhibitor of tyrosinase for biosynthesis of melanin in melanocytes, was investigated in human transfectant HaCaT and SCC-13 cells. These two keratinocyte cell lines transfected with pNF-kappaB-SEAP-NPT plasmid were used to determine the activation of NF-kappaB. Transfectant cells release the secretory alkaline phosphatase (SEAP) as a transcription reporter in response to the NF-kappaB activity and contain the neomycin phosphotransferase (NPT) gene for the dominant selective marker of geneticin resistance. NF-kappaB activation was measured in the SEAP reporter gene assay using a fluorescence detection method. Kojic acid showed the inhibition of cellular NF-kappaB activity in both human keratinocyte transfectants. It could also downregulate the ultraviolet ray (UVR)-induced activation of NF-kappaB expression in transfectant HaCaT cells. Moreover, the inhibitory activity of kojic acid in transfectant HaCaT cells was found to be more potent than known antioxidants, e.g., vitamin C and N-acetyl-L-cysteine. These results indicate that kojic acid is a potential inhibitor of NF-kappaB activation in human keratinocytes, and suggest the hypothesis that NF-kappaB activation may be involved in kojic acid induced anti-melanogenic effect.

Moon KY et al; Arch Pharm Res 24 (4): 307-11 (2001):