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2D Structure
Also known as: 96-24-2, 3-chloropropane-1,2-diol, Alpha-chlorohydrin, Chlorodeoxyglycerol, Epibloc, Glycerol alpha-monochlorohydrin
Molecular Formula
C3H7ClO2
Molecular Weight
110.54  g/mol
InChI Key
SSZWWUDQMAHNAQ-UHFFFAOYSA-N
FDA UNII
QGS78A3T6P

A chlorinated PROPANEDIOL with antifertility activity in males used as a chemosterilant in rodents.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-chloropropane-1,2-diol
2.1.2 InChI
InChI=1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2
2.1.3 InChI Key
SSZWWUDQMAHNAQ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(C(CCl)O)O
2.2 Other Identifiers
2.2.1 UNII
QGS78A3T6P
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3 Chloro 1,2 Propanediol

2. 3 Chloropropanediol

3. 3 Monochloropropane 1,2 Diol

4. 3-chloropropanediol

5. 3-mcpd

6. 3-monochloropropane-1,2-diol

7. Alpha Chlorhydrin

8. Alpha Chlorohydrin

9. Alpha-chlorhydrin

10. Alpha-chlorohydrin

11. Alpha-monochlorohydrin, Glycerol

12. Glycerol Alpha Monochlorohydrin

13. Glycerol Alpha-monochlorohydrin

14. U 5897

15. U-5897

16. U5897

2.3.2 Depositor-Supplied Synonyms

1. 96-24-2

2. 3-chloropropane-1,2-diol

3. Alpha-chlorohydrin

4. Chlorodeoxyglycerol

5. Epibloc

6. Glycerol Alpha-monochlorohydrin

7. 1,2-propanediol, 3-chloro-

8. Chloropropanediol

9. A-chlorohydrin

10. 3-chloropropanediol

11. 3-chloropropylene Glycol

12. Glycerol Chlorohydrin

13. Glyceryl Chloride

14. 1-chloro-2,3-dihydroxypropane

15. 1-chloropropane-2,3-diol

16. Alpha-chlorohydrine

17. Chlorohydrin

18. Monochlorohydrin

19. 3-mcpd

20. 1-chloro-2,3-propanediol

21. Glycerin Epichlorohydrin

22. Glycerol 3-chlorohydrin

23. 2,3-dihydroxypropyl Chloride

24. 1-chloro-1-deoxyglycerol

25. Alpha-monochlorohydrin

26. 3-chloro-1,2-dihydroxypropane

27. U 5897

28. 1,2-dihydroxy-3-chloropropane

29. 3-chloro-1,2-propylene Glycol

30. Glyceryl Alpha-chlorohydrin

31. Glyceryl-alpha-chlorohydrin

32. (rs)-3-chloro-1,2-propanediol

33. .alpha.-chlorohydrin

34. Glycerin Alpha-monochlorhydrin

35. (+/-)-3-chloro-1,2-propanediol

36. 3-monochloro-1,2-propanediol

37. 3-monochloropropane-1,2-diol

38. 1,2-propanediol, 3-dichloro-

39. (+-)-2,3-dihydroxychloropropane

40. 3-chloro-1,2-propandiol

41. A-monochlorohydrin

42. Beta,beta'-dihydroxyisopropyl Chloride

43. U-5897

44. Chloropropylene Glycol

45. A-glycerol Chlorohydrin

46. Chloro-1,2-propanediol

47. Chloro-1,2-dihydroxypropane

48. Qgs78a3t6p

49. Glycerine Alpha-monochlorohydrin

50. Glycerin .alpha.-monochlorhydrin

51. Chebi:18721

52. Chlorhydrin

53. Monochlorhydrin

54. Dsstox_cid_664

55. Dsstox_rid_75718

56. 3-chloro-propane-1,2-diol

57. Dsstox_gsid_20664

58. Caswell No. 214a

59. Ekorod A

60. (s)-( )-3-chloro-1,2-propanediol

61. Cas-96-24-2

62. Ccris 4607

63. Hsdb 2052

64. Einecs 202-492-4

65. Un2689

66. 3-mcdp

67. Unii-qgs78a3t6p

68. Epa Pesticide Chemical Code 117101

69. Brn 0635684

70. Ai3-11200

71. U5897

72. (2r)-(-)-3-chloropropane-1,2-diol

73. (2s)-(+)-3-chloropropane-1,2-diol

74. Mfcd00004712

75. Chlorohydrin-

76. .alpha.-monochlorohydrine

77. 3-chloro1,2-propanediol

78. Alpha-glycerol Chlorohydrin

79. Glycerol A-monochlorohydrin

80. (+/-)-alpha-chlorohydrin

81. Ec 202-492-4

82. 3-chloro-1,2-propan-diol

83. Glycerol Alpha -chlorohydrin

84. Glyceryl Alpha -chlorohydrin

85. 3-chloropropandiol-(1,2)

86. 3-chloro-1,2-propane Diol

87. 3-chloro-1,2-propane-diol

88. Schembl19213

89. 3-dichloro-1,2-propanediol

90. 4-01-00-02484 (beilstein Handbook Reference)

91. Glycerol .alpha.-chlorohydrin

92. Glyceryl .alpha.-chlorohydrin

93. Mls000028887

94. Glycerin Alpha -monochlorhydrin

95. .alpha.-monochlorohydrin

96. Dl-.alpha.-chlorohydrin

97. Glycerol-alpha -monochlorohydrin

98. Chembl3185949

99. Dtxsid4020664

100. 3-chloro-1,2-proandiol

101. Glycerol-.alpha.-monochlorohydrin

102. Racemic 3-chloro-1,2-propanediol

103. .alpha.-chlorohydrin [mi]

104. 3-chloro-1,2-dihydroxy-n-propane

105. Act05631

106. Amy21866

107. Bcp31835

108. Tox21_202262

109. Tox21_302959

110. Bbl011374

111. Stl146471

112. Akos000121375

113. (.+/-.)-2,3-dihydroxychloropropane

114. Sb44720

115. Un 2689

116. .alpha.-chlorohydrin, (+/-)-

117. Ncgc00249201-01

118. Ncgc00256557-01

119. Ncgc00259811-01

120. Smr000059152

121. Vs-02932

122. (+/-)-2,3-dihydroxychloropropane

123. (+/-)-3-chloro-1,2-propanediol, 98%

124. .beta.,.beta.'-dihydroxyisopropyl Chloride

125. Db-028420

126. (s)-acetylthio-3-phenylpropionicacid

127. 3-chloro-1,2-propanediol Monochlorhydrin

128. Ft-0605055

129. Ft-0605261

130. 3-chloropropane-1,2-diol;chlorodeoxyglycerol

131. C18676

132. Q223066

133. 3-chloropropylene Glycol. Epibloc (pestcon)

134. (+/-)-3-chloro-1,2-propanediol, Analytical Standard

135. 3-chloro-1,2-propanediol 100 Microg/ml In Methanol

136. 3-chloro-1,2-propanediol 100 Microg/ml In Acetonitrile

137. 3-chloro-1,2-propanediol 100 Microg/ml In Ethyl Acetate

138. (+/-)-3-chloro-1,2-propanediol, Purum, >=98.0% (gc)

139. Glycerol Alpha-monochlorohydrin [un2689] [keep Away From Food]

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 110.54 g/mol
Molecular Formula C3H7ClO2
XLogP3-0.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass110.0134572 g/mol
Monoisotopic Mass110.0134572 g/mol
Topological Polar Surface Area40.5 Ų
Heavy Atom Count6
Formal Charge0
Complexity32
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Chemosterilants

Compounds that cause reproductive sterility in organisms. They are sometimes used to control pest populations by sterilizing males within the population. (See all compounds classified as Chemosterilants.)


4.2 Metabolism/Metabolites

FOLLOWING ADMIN OF ALPHA-CHLOROHYDRIN (100 MG/KG, IP) TO MALE RATS, BETA-CHLOROLACTIC ACID & OXALIC ACID WERE ISOLATED FROM URINE.

JONES AR ET AL; XENOBIOTICA 8(9) 573 (1978)


4.3 Mechanism of Action

Glycidol ... an industrial chemical, has been showed to be a reproductive toxicant in short term studies and a carcinogen in rats and mice in /carcinogenicity/ studies. The reproductive toxicity of glycidol was believed to result from its conversion to alpha-chlorohydrin by the action of hydrochloric acid in the stomach. The comparative disposition of glycidol was investigated in rats following oral or iv admin at doses of 37.5 and 75 mg/kg. ... Approx 87-92% of the dose was absorbed from the gastrointestinal tract of the rat. (14)C-Glycidol equivalents were eliminated in urine (40-48% of the dose in 72 hr), feces (5-12%), and exhaled as CO2 (26-32%). At both doses, 9-12% and 7-8% (estimated) of the dose remained in tissues at 24 or 72 hr following dosing, respectively. In general, the concn of glycidol equivalents in tissues were proportional to the dose. The highest concn of radioactivity were /noted/ in the blood cells, thyroid, liver, kidney, spleen, and the lowest in adipose tissue, skeletal muscle, and plasma. The pattern of distribution of radioactivity in tissues was similar for both the iv and oral routes. The total recovery of radioactivity ranged from 87 to 91% of the dose. Urinary radioactivity was resolved by HPLC analysis into 15 metabolites. There were one major (14-21% of the dose) and four lesser metabolites (each representing 2-8%); the others were minor, each representing 1% or less of the dose. In general, the urinary metabolic profile was similar to iv or oral admin of the two doses studied. ...

Nomeir AA et al; J Toxicol Environ Hlth 44 (2): 203-17 (1995)


The ultrastructural changes of each epididymal segment of the rat were brought about by alpha-chlorohydrin (20 mg/kg/day, for successive five times). The alteration appeared in proper order from initial segment to caudal segment, and the digression in profundity and range got less serious as the distance to the testis increased. This alteration disappeared gradually as the time went by. The recovery process also began at initial segment but its cycle was shortened gradually from initial segment to caudal segment. These results showed the factor that caused the above mentioned processes stemmed from the testis chiefly and was in epididymal plasma. It affected each epididymal segment along the epididymal lumen and to the injury of the epididymal epithelium; at the same time, the concentration of the factor became more decreased. The relationship between the antifertility effect of alpha-chlorohydrin and the ... ultrastructural changes of the epididymis and the mechanism of the double effects depending on dose of alpha-chlorohydrin were discussed.

Luo S et al; Acta Acad Med Hubei 12 (2): 120-5 (1991)


An acute phase of severe hepatic necrosis induced by dichloropropanol was examined immunohistochemically and ultrastructurally, in order to study chronological changes of sinusoidal morphology during acute hepatic injury. Male wistar rats were injected with 1,3-dichloro-2-propanol (DC2P) and sacrificed at various intervals after the injections. DC2P injected rats showed zonal necrosis of the centrilobular space with a peak from 24 to 48 hr after the injection. Destruction of sinusoidal linings appeared at 4 hr, and was gradually aggravated along the advancing hepatocytic necrosis. Monocytic influx into the necrotic areas was initiated at 6 hr. At 48 hr, collapsed centrilobular spaces showed a loss of most sinusoidal structures with active phagocytosis of macrophages, proliferation of perisinusoidal cells and accumulation of collagen fibrils. At 72 hr, there were many regenerating sinusoidal structures, which were composed of rather thick and less fenestrated endothelium and underlying multilayered processes of mesenchymal cells, along the regenerating hepatocytes. In these areas, occasional junctions between regenerating hepatocytes and mesenchymal cells were /observed/. Reconstruction of sinusoidal linings was closely related to the hepatocytic regeneration, and a hepatocytic mesenchymal interaction might participate in this morphodynamic course of the sinusoidal reconstruction.

PMID:8196516 Harataka J et al; Liver 14 (2): 90-7 (1994)