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Beta-Glucono-1,5-Lactone

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Synopsis

ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Delta-gluconolactone, 90-80-2, D-glucono-1,5-lactone, Gluconic acid lactone, D-gluconolactone, 1,5-gluconolactone

Molecular Formula

C₆H₁₀O₆

Molecular Weight

178.14 g/mol

InChI Key

PHOQVHQSTUBQQK-SQOUGZDYSA-N

FDA UNII

WQ29KQ9POT

Gluconolactone is a naturally occurring polyhydroxy acid (PHA) with metal chelating, moisturizing and antioxidant activity. Gluconolactone can be produced by enzymatic oxidation of D-glucose oxidation. Its ability in free radicals scavenging accounts for its antioxidant property. It is used in cosmetic product and as a coagulant in tofu processing. (NCI05)

Gluconolactone is a Calculi Dissolution Agent. The mechanism of action of gluconolactone is as an Irrigation.

1 2D Structure

Beta-Glucono-1,5-Lactone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one

2.1.2 InChI

InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1

2.1.3 InChI Key

PHOQVHQSTUBQQK-SQOUGZDYSA-N

2.1.4 Canonical SMILES

C(C1C(C(C(C(=O)O1)O)O)O)O

2.1.5 Isomeric SMILES

C([C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

WQ29KQ9POT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Beta-glucono-1,5-lactone

2. Delta-gluconolactone

3. Gdl (gluconate)

4. Gluconic Lactone

5. Glucono-delta-lactone

6. Gulonic Acid Gamma-lactone

2.3.2 Depositor-Supplied Synonyms

1. Delta-gluconolactone

2. 90-80-2

3. D-glucono-1,5-lactone

4. Gluconic Acid Lactone

5. D-gluconolactone

6. 1,5-gluconolactone

7. Glucono Delta-lactone

8. D-(+)-glucono-1,5-lactone

9. D-gluconic Acid Lactone

10. D-gluconic Acid Delta-lactone

11. 1,5-d-gluconolactone

12. (3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-one

13. Gluconic Lactone

14. Glucono Delta Lactone

15. Gluconic Delta-lactone

16. Fujiglucon

17. D-delta-gluconolactone

18. Delta-d-gluconolactone

19. Deltagluconolactone

20. (3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one

21. D-gluconic Delta-lactone

22. D-(+)-gluconic Acid Delta-lactone

23. Glucarolactone

24. Glucono-delta-lactone

25. D-aldonolactone

26. Beta-glucono-1,5-lactone

27. D-gluconic Acid-delta-lactone

28. Gluconolactone [usp]

29. Lysactone

30. Riken Lactone

31. D-threo-aldono-1,5-lactone

32. 1335-57-5

33. Ai3-19578

34. Gluconic Acid Anhydride

35. Gluconic Acid, Delta-lactone, D-

36. Glucono .delta. Lactone

37. Glucono .delta.-lactone

38. .delta.-d-gluconolactone

39. Wq29kq9pot

40. 4253-68-3

41. Gluconic Acid Delta-lactone

42. Ins No.575

43. Chebi:16217

44. D-gluconic Acid .delta.-lactone

45. Ins-575

46. Nsc-34393

47. Nsc-758238

48. Gluconolactone (usp)

49. E-575

50. Nsc 34393

51. Dsstox_cid_6549

52. (3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one

53. Dsstox_rid_78147

54. Dsstox_gsid_26549

55. 135820-79-0

56. D-gluconic Acid, .delta.-lactone

57. Glucolactone

58. D-gluconic Acid D-lactone

59. (3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2h-pyran-2-one

60. Cas-90-80-2

61. .delta.-gluconolactone

62. D-glucono-delta-lactone

63. Lgc

64. Hsdb 488

65. D-gluconic Acid-1,5-lactone

66. Einecs 202-016-5

67. Unii-wq29kq9pot

68. Gluconic Acid Lactone (6ci)

69. Nsc34393

70. Delta-gluconic Acid Delta-lactone

71. Glucono--lactone

72. Gluconodeltalactone

73. Delta-aldonolactone

74. Gluconate, Lactone

75. Ncgc00095002-01

76. Delta Gluconolactone

77. Gamma-gluconolactone

78. Gdl

79. D-glucono-d-lactone

80. Mfcd00006647

81. Glucono Gamma-lactone

82. Glucono-1,5-lactone

83. Glucono 1,5-lactone

84. D-glucono1,5-lactone

85. Gluconic Acid D-lactone

86. Delta-delta-gluconolactone

87. 1,5-delta-gluconolactone

88. Bmse000230

89. Delta-gluconic Acid Lactone

90. Delta-glucono-delta-lactone

91. Ec 202-016-5

92. Gluconolactone [ii]

93. Gluconolactone [mi]

94. Delta-glucono-1,5-lactone

95. Delta-gluconic Delta-lactone

96. Glucono-delta-lactone(gdl)

97. Schembl15320

98. Gluconolactone [hsdb]

99. Gluconolactone [inci]

100. Delta-gluconic Acid D-lactone

101. Mls002207105

102. D-gluconic Acid 1,5-lactone

103. Gluconolactone [mart.]

104. Gluconolactone [usp-rs]

105. Gluconolactone [who-dd]

106. Chembl1200829

107. D-(+)-gluconic Acid D-lactone

108. Dtxsid0026549

109. Delta-gluconic Acid 1,5-lactone

110. Delta-gluconic Acid-1,5-lactone

111. Delta-gluconic Acid-delta-lactone

112. D(+)-gluconic Acid Gamma-lactone

113. Glucono-

114. A-lactone Usp26 Fcciv

115. Cs-m3768

116. D-(+)-gluconic Acid-delta Lactone

117. Delta-(+)-gluconic Acid D-lactone

118. Glucono Delta-lactone [fcc]

119. Hy-i0301

120. Zinc2539702

121. Gluconolactone [orange Book]

122. Tox21_111383

123. Tox21_200429

124. Bdbm50366565

125. Glucono-delta-lactone [vandf]

126. Gluconolactone [usp Monograph]

127. Akos016843888

128. Tox21_111383_1

129. Db04564

130. Delta-(+)-gluconic Acid-delta Lactone

131. Ds-4779

132. Ncgc00257983-01

133. Ncgc00344522-01

134. Renacidin Component Gluconolactone

135. Ac-13150

136. E575

137. Smr001306715

138. Gluconolactone Component Of Renacidin

139. G0039

140. C00198

141. D04332

142. P19765

143. D-(+)-gluconic Acid Delta-lactone, >=99.0%

144. Gluconolactone, Meets Usp Testing Specifications

145. Q114174

146. W-100325

147. 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one

148. 3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one

149. D-(+)-gluconic Acid Delta-lactone, Analytical Standard

150. Wurcs=2.0/1,1,0/[a2122h_1-5]/1/

151. A88519cb-a562-4c9c-b925-0a6b1701f841

152. Gluconolactone, United States Pharmacopeia (usp) Reference Standard

153. (3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydropyran-2-one

154. (3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-one (non-preferred Name)

155. (3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-one; Gluconolactone

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₆H₁₀O₆
Molecular Weight	178.14 g/mol
XLogP3	-2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	1
Exact Mass	178.04773803 g/mol
Monoisotopic Mass	178.04773803 g/mol
Topological Polar Surface Area	107 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	181
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

MEDICATION (VET): ...Mixture in urine helps dissolve urinary tract stones containing calcium carbonate, tricalcium phosphate, calcium oxalates, & magnesium ammonium phosphates but usually none containing uric acid, urates, cystineine, or some oxalates.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 240

MEDICATION (VET): 0.5% Solution can be used for irrigating the urethra & bladder when indicated. Similar strength as a rinse can help maintain in dwelling urethral catheters free of calcification.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 240

5 Pharmacology and Biochemistry

5.1 FDA Pharmacological Classification

5.1.1 Active Moiety

GLUCONOLACTONE

5.1.2 FDA UNII

WQ29KQ9POT

5.1.3 Pharmacological Classes

Mechanisms of Action [MoA] - Irrigation

FDF Dossiers