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Chemistry

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Also known as: Butane-1,3-diol, 107-88-0, 1,3-butylene glycol, Butylene glycol, 1,3-dihydroxybutane, Methyltrimethylene glycol
Molecular Formula
C4H10O2
Molecular Weight
90.12  g/mol
InChI Key
PUPZLCDOIYMWBV-UHFFFAOYSA-N
FDA UNII
3XUS85K0RA

1,3-Butanediol
RN given refers to cpd without isomeric designation
1 2D Structure

1,3-Butanediol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
butane-1,3-diol
2.1.2 InChI
InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3
2.1.3 InChI Key
PUPZLCDOIYMWBV-UHFFFAOYSA-N
2.2 Other Identifiers
2.2.1 UNII
3XUS85K0RA
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,3-butylene Glycol

2. Butylene Glycol

2.3.2 Depositor-Supplied Synonyms

1. Butane-1,3-diol

2. 107-88-0

3. 1,3-butylene Glycol

4. Butylene Glycol

5. 1,3-dihydroxybutane

6. Methyltrimethylene Glycol

7. 1,3 Butylene Glycol

8. 1,3-butandiol

9. Beta-butylene Glycol

10. 1-methyl-1,3-propanediol

11. (rs)-1,3-butandiol

12. 1,3-butylenglykol

13. Caswell No. 128gg

14. Nsc-402145

15. Dtxsid8026773

16. 3xus85k0ra

17. Brn 1731276

18. Chebi:52683

19. Ai3-11077

20. Dtxcid306773

21. Nsc402145

22. Herbal Moxibustion

23. Chinese Medicine Patch

24. Mummy Mask

25. Refchem:54584

26. Glytoucan:g07075bd

27. 3% Hyaluronic Acid Serum

28. Natural Oriental Herb Care

29. Srripo Biotin Hair Treatment

30. Acmeros Lubricant X0026f3541

31. Shizhentaiyitang Moxibustion Patch

32. Linglongjiuhuo Linglong Moxibustion

33. Qizhouguai Chinese Medicine Patch

34. G07075bd

35. Vshell Hair Treatment Biotin Conditioner

36. 3ce Super Slim Pen Eye Liner Black

37. 3ce Super Slim Pen Eye Liner Brown

38. Water-based Personal Lubricant, Acvioo 001

39. 3ce Super Slim Pen Eye Liner Light Brown

40. 3ce Super Slim Pen Eye Liner Burgundy Brown

41. Linglongjiuhuo Linglong Moxibustion Wormwood Moxibustion Patch

42. 203-529-7

43. (+/-)-1,3-butanediol

44. 1,3-butanodiol

45. Mfcd00004554

46. .beta.-butylene Glycol

47. Bd

48. Nsc 402145

49. ( Inverted Exclamation Marka)-1,3-butanediol

50. Butanediol,1,3-

51. Nsc6966

52. 1,3-butandiol [german]

53. 1,3-butane Diol

54. Cas-107-88-0

55. 1,3-butylenglykol [german]

56. Hsdb 153

57. 1,3-butanediol, (r)-

58. 1,3-butanediol, (s)-

59. Einecs 203-529-7

60. Unii-3xus85k0ra

61. (s)-(+)-1,3-butylene Glycol

62. B-butylene Glycol

63. 1.3-butanediol

64. 1,3 -butanediol

65. Utane-1,3-diol

66. Butylene Glycol (butane-1,3-diol)

67. Dl-1,3-butanediol

68. R-butane-1,3-diol

69. Butylene Glycol (nf)

70. Racemic 1,3-butanediol

71. Butanediol,3-

72. 1,3-butanediol, Dl-

73. (rs)-1,3-butanediol

74. 1,3-butanediol 100 Microg/ml In Acetonitrile

75. Ec 203-529-7

76. Schembl8176

77. (+/-) 1,3 Butandiol

78. (+/-)-1,3-butandiol

79. 1,3-butanediol (standard)

80. Schembl19355

81. Schembl94448

82. Butylene Glycol [ii]

83. 0-01-00-00477 (beilstein Handbook Reference)

84. Schembl331940

85. Schembl739193

86. Orb1298236

87. Schembl1044624

88. Schembl1547914

89. Schembl1749188

90. Schembl2688282

91. Schembl8023169

92. (.+/-.)-1,3-butanediol

93. Chembl3186475

94. Wln: Qy1 & 2q

95. (s)-(+)-1,3-butane Diol

96. 1,3-butanediol [hsdb]

97. 1,3-butandiol [who-dd]

98. Hy-77490ar

99. 1,3-butanediol, (.+/-.)-

100. 1,3-butylene Glycol [mi]

101. Nsc-6966

102. 1,3-butylene Glycol [fcc]

103. Tox21_202408

104. Tox21_300085

105. 1,3 Butylene Glycol [fhfi]

106. Bbl037424

107. Butane-1,3-diol [usp-rs]

108. Hy-77490a

109. Stl483070

110. Akos000119043

111. Db14110

112. Fb31081

113. Msk002151-100m

114. Sb44648

115. Sb44659

116. Sb83779

117. Ncgc00247900-01

118. Ncgc00247900-02

119. Ncgc00253944-01

120. Ncgc00259957-01

121. Sy009940

122. 1,3 Butylene Glycol, (+/-)-

123. Db-000434

124. Db-011642

125. (+/-)-1,3-butanediol, Analytical Standard

126. B0679

127. B3770

128. Cs-0115644

129. Ns00008159

130. En300-19320

131. (+/-)-1,3-butanediol, Anhydrous, >=99%

132. C20335

133. D10695

134. F82621

135. 1,3-butanediol Solution In Methanol, 100ug/ml

136. F099380

137. Q161496

138. (+/-)-1,3-butanediol, Reagentplus(r), 99.5%

139. (+/-)-1,3-butanediol, Reagentplus(r), >=99.0%

140. (+/-)-1,3-butanediol, Saj First Grade, >=98.0%

141. (+/-)-1,3-butanediol, Vetec(tm) Reagent Grade, 98%

142. F8880-3340

143. Butane-1,3-diol, United States Pharmacopeia (usp) Reference Standard

144. 55251-78-0

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 90.12 g/mol
Molecular Formula C4H10O2
XLogP3-0.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area40.5
Heavy Atom Count6
Formal Charge0
Complexity28.7
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

/EXP THER/ This study examined the effect of 1,3-butanediol on the selective loss of CA1 pyramidal neurons following a short period of near-complete forebrain ischemia. Injection of 55 mmol 1,3-butanediol/kg body weight at 24 h of recirculation and again at 36 hr following 10 min of forebrain ischemia markedly reduced damage to CA1 neurons examined at 72 hr of recirculation compared with that in saline-treated rats. Comparable treatment with ethanol did not cause significant protection. Neuronal loss was also not reduced by 1,3-butanediol treatment when the ischemic period was extended to 15 min or by single treatments at 24 hr or 36 hr following 10 min of ischemia. However, a single treatment 5 min after reversal of 10 min of ischemia was effective in ameliorating cell loss. The difference in effectiveness of 1,3-butanediol following 10 min and 15 min of ischemia is consistent with a number of previous studies, indicating that the processes leading to loss of CA1 neurons are modified when the ischemic period is extended. Previous findings that 1,3-butanediol reduced damage in other ischemia-susceptible neuronal subpopulations but not in CA1 neurons most likely reflected the longer period of ischemia which was used. The results of the present investigation demonstrate that administration of 1,3-butanediol offers a novel approach for interfering with post-ischemic loss of CA1 neurons following a brief ischemic period which is effective even when initiated after prolonged recirculation periods.

PMID:7859074 Sims NR et al; Brain Res. 662(1-2):216-22 (1994)


/EXP THER/ The biochemical effect of S-1,3-butanediol on streptozotocin induced diabetic rats was studied. Rats were made diabetic by the intraperitoneal injection of 40 mg/kg body weight streptozotocin in sodium citrate buffer. A dosage of 25 mmol/kg body weight of S-1,3-butanediol was injected intraperitoneally for treatment. The streptozotocin induced diabetic rats showed a marked increase in blood glucose level, and significant increase in the level of cholesterol, triglycerides and free fatty acids. The glycogen levels in liver and kidney were greatly decreased in diabetic rats. Treatment with butanediol normalized the glucose and glycogen level but had no significant effect on protein and lipid levels.

Meenakshi C et al; Indian J Physiol Pharmacol. 1995 Apr;39(2):145-8


/EXP THER/ We previously showed that intrastriatal administration of aminooxyacetic acid (AOAA) produces striatal lesions by a secondary excitotoxic mechanism associated with impairment of oxidative phosphorylation. In the present study, we show that and the specific complex I inhibitor rotenone produces a similar neurochemical profile in the striatum, consistent with an effect of AOAA on energy metabolism. Lesions produced by AOAA were dose-dependently blocked by MK-801, with complete protection against GABA and substance P depletions at a dose of 3 mg/kg. AOAA lesions were significantly attenuated by pretreatment with either 1,3-butanediol or coenzyme Q10, two compounds which are thought to improve energy metabolism. These results provide further evidence that AOAA produces striatal excitotoxic lesions as a consequence of energy depletion and they suggest therapeutic strategies which may be useful in neurodegenerative diseases.

PMID:7824183 Brouillet E et al; Neurosci Lett 177(1-2):58-62 (1994)


/EXP THER/ In order to assess the therapeutic value of 1,3 butanediol in ethylene glycol toxicosis, mixed-bred dogs were given an oral dose of commercial antifreeze at 6 mL/kg of body weight (0 hour) and treated (IV) 7 times at 6-hour intervals with 5.5 mL/kg of body weight 1,3 butanediol solution (20% in physiological saline solution) beginning at 8, 12, and 21 hours. Serum glycolic acid concentration was quantitated by high-pressure liquid chromatography. Three dogs that were given ethylene glycol, but no 1,3 butanediol treatment, died with elevated serum glycolic acid concentrations. Five dogs were given ethylene glycol and 1,3 butanediol treatment. Of 2 dogs treated at 8 hours, 1 survived and 1 died at 39 hours; 1 treated at 12 hours and 1 treated at 21 hours survived; 1 dog died soon (27 hours) after treatment was initiated at 21 hours. Four of the 5 dogs had dramatically decreased serum glycolic acid concentrations after 1,3 butanediol treatment, indicating its effectiveness in inhibiting alcohol dehydrogenase-dependent glycolic acid formation in vivo.

Murphy MJ et al; Am J Vet Res. 45(11):2293-5 (1984)


/EXP THER/ Pre-partum feeding of 1,3-butanediol to sows has been shown to improve the metabolic status and survival rate of neonatal pigs. To evaluate the efficacy of short-term, pre-partum feeding of 1,3-butanediol on pig and sow productivity on a large scale and low concentration was the focus of the research. The secondary objective was to determine if pre-partum feeding of 1,3-butanediol had any effect on survival rate and weight gain of lesser body weight pigs, sow body weight and subsequent sow reproductive performance. In a large commercial unit, 2537 sows were fed one of two pre-partum diets (0% or 4.55% 1,3-butanediol) on Day 108+/-3 of pregnancy. 1,3-butanediol provided 8% of the total metabolizable energy. Pigs born live in those litters were equalized by cross-fostering among sows receiving the same pre-partum diet. Pigs were weaned from the sows at 16+/-3 days post-partum and return of sows to estrus and conception rates were determined. Pre-partum feeding of 1,3-butanediol reduced (P=0.01) pre-weaning pig mortalities from 1.44 to 1.24 pigs per litter. The reduction in pig mortality was independent of length of 1,3-butanediol feeding (4 to 11 days). In a subset of 750 litters, four lesser birth-weight pigs from each litter were tagged and monitored to determine the effect of 1,3-butanediol on survival rates and pre-weaning weight gain of pigs with the greatest mortality risk. 1,3-butanediol reduced (P=0.01) pre-weaning mortality of these low birth weight pigs by 5.27%. Based on these data, short-term pre-partum feeding of 1,3-butanediol effectively improves pre-weaning pig productivity at a lower concentration than previously reported.

Stahly TS et al; Anim Reprod Sci. 148 (3-4):145-52 (2014)


5 Pharmacology and Biochemistry
5.1 Metabolism/Metabolites

Butanediol is metabolized by the liver... beta-hydroxybutyric acid /a main metabolite/ is further metabolized in the tricarboxylic acid cycle to carbon dioxide, which accounts for about 90% of the dose administered. In other studies... in which rats were fed 1,3-butanediol for 3 to 7 weeks, it was found that the blood level of beta-hydroxybutyrate, was also higher than normal.

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 45


R- and S-1,3-butylene glycol are taken up by the isolated liver of fed or starved rats at the same rate. R-1,3-butylene glycol is mainly transformed to the physiological ketone bodies R-3-hydroxybutyrate and acetoacetate. Only 29-38&% of the S-enantiomer are converted into physiological ketone bodies. The S-enantiomer is further metabolised to S-3-hydroxybutyrate (not a natural compound), lipids and carbon dioxide. Based on these results it can be concluded that the test item is metabolised via physiological pathways, suggesting that it has a low potential to accumulate.

ECHA; REACH Registration for butane-1,3-diol (CAS 107-88-0); Available from, as of November 5, 2015: https://echa.europa.eu/


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