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Chemistry

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Also known as: Butanol, Butan-1-ol, N-butanol, Butyl alcohol, 71-36-3, N-butyl alcohol
Molecular Formula
C4H10O
Molecular Weight
74.12  g/mol
InChI Key
LRHPLDYGYMQRHN-UHFFFAOYSA-N
FDA UNII
8PJ61P6TS3

butanol
A four carbon linear hydrocarbon that has a hydroxy group at position 1.
1 2D Structure

butanol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
butan-1-ol
2.1.2 InChI
InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
2.1.3 InChI Key
LRHPLDYGYMQRHN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCO
2.2 Other Identifiers
2.2.1 UNII
8PJ61P6TS3
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1 Butanol

2. Alcohol, Butyl

3. Alcohol, N-butyl

4. Butyl Alcohol

5. N Butanol

6. N Butyl Alcohol

7. N-butanol

8. N-butyl Alcohol

2.3.2 Depositor-Supplied Synonyms

1. Butanol

2. Butan-1-ol

3. N-butanol

4. Butyl Alcohol

5. 71-36-3

6. N-butyl Alcohol

7. 1-hydroxybutane

8. Propylcarbinol

9. Butyl Hydroxide

10. Methylolpropane

11. Propylmethanol

12. Hemostyp

13. Butyric Alcohol

14. N-butan-1-ol

15. 1-butyl Alcohol

16. Butanolo

17. Propyl Carbinol

18. Alcool Butylique

19. Butylowy Alkohol

20. Buoh

21. Butanolen

22. Normal Primary Butyl Alcohol

23. Rcra Waste Number U031

24. Ccs 203

25. N-buoh

26. Fema No. 2178

27. Butyric Or Normal Primary Butyl Alcohol

28. N-butylalkohol

29. Butanol-1

30. N-propyl Carbinol

31. 35296-72-1

32. Nsc 62782

33. Butyl Alcohol (nf)

34. Butyl Alcohol [nf]

35. Mfcd00002964

36. Chembl14245

37. 8pj61p6ts3

38. Chebi:28885

39. Nsc-62782

40. Ncgc00090961-02

41. Butanols

42. Dsstox_cid_1740

43. Butanol [french]

44. Dsstox_rid_76300

45. Dsstox_gsid_21740

46. Butanolen [dutch]

47. Butanolo [italian]

48. 1-butanol, Analytical Standard

49. Butyl Alcohol (natural)

50. Fema Number 2178

51. Alcohol, Butyl

52. Alcool Butylique [french]

53. Butylowy Alkohol [polish]

54. 1 Butanol

55. 1-butanol, Acs Reagent, >=99.4%

56. Cas-71-36-3

57. 1bo

58. Hsdb 48

59. Butanol, 1-

60. Ccris 4321

61. Einecs 200-751-6

62. Rcra Waste No. U031

63. Unii-wb09ny83ya

64. Butaneol

65. Butylalcohol

66. Unii-8pj61p6ts3

67. Butyl-alcohol

68. N-butylalcohol

69. Normal Butanol

70. 1-butylalcohol

71. Ai3-00405

72. N-butanolbutanolen

73. Nbuoh

74. 1 -butanol

75. 1- Butanol

76. 1-n-butanol

77. 1-butanol, Anhydrous

78. Alcohol,butyl

79. N-butyl Alcohol,(s)

80. 1-butanol, For Hplc

81. N-butanol, Hplc Grade

82. 1-butanol, 99%

83. 1-butanol, Hplc Grade

84. N-c4h9oh

85. Bmse000447

86. Na 1120 (related)

87. 1-butanol, 99.9%

88. Ec 200-751-6

89. Butyl Alcohol [ii]

90. Butyl Alcohol [fcc]

91. Wb09ny83ya

92. Butyl Alcohol [fhfi]

93. Butyl Alcohol [hsdb]

94. Wln: Q4

95. 1-butanol [usp-rs]

96. Alcohol,butyl [vandf]

97. Bidd:er0611

98. N-butyl Alcohol [mi]

99. Nat. Butanol (butyl Alcohol)

100. Aqualine™ Standard 5.1

101. Butyl Alcohol [mart.]

102. N-butyl Alcohol [inci]

103. 1-butanol, Lr, >=99%

104. Aqualine™ Standard 10.1

105. Dtxsid1021740

106. Bdbm36173

107. Butyl Alcohol (fragrance Grade)

108. Butyl Alcohol Reagent Grade Acs

109. 1-butanol, Anhydrous, 99.8%

110. Butyl Alcohol (industrial Grade)

111. N-butanol, Acs, 99.4+%

112. N-butyl Alcohol [who-dd]

113. 1-butanol, Ar, >=99.5%

114. 1-butanol, For Hplc, 99.8%

115. Butyl Alcohol, >=99.9%, Fcc

116. Nsc62782

117. Zinc1530354

118. Tox21_111046

119. Tox21_200741

120. Lmfa05000109

121. Stl264186

122. Akos000249218

123. Zinc100492542

124. 1-butanol 100 Microg/ml In Methanol

125. 1-butanol 500 Microg/ml In Methanol

126. 1-butanol, For Hplc, >=99.7%

127. Db02145

128. 1-butanol 1000 Microg/ml In Methanol

129. Butyl Alcohol, >=99.9%, Fcc, Fg

130. Ncgc00090961-01

131. Ncgc00090961-03

132. Ncgc00258295-01

133. 1-butanol 100 Microg/ml In Acetonitrile

134. Bp-30034

135. 1-butanol, Saj First Grade, >=99.0%

136. 1-butanol, For Molecular Biology, >=99%

137. 1-butanol, Jis Special Grade, >=99.0%

138. 1-butanol, P.a., Acs Reagent, 99.4%

139. 1-butanol, For Hplc, >=99.8% (gc)

140. 1-butanol, Spectrophotometric Grade, 99.5%

141. 1-butanol, Uv Hplc Spectroscopic, 99.5%

142. B0228

143. B0704

144. B0944

145. Ft-0607555

146. Ft-0623296

147. Ft-0774976

148. 1-butanol, Anhydrous, Zero2(tm), 99.8%

149. 1-butanol, Ultrapure, Spectrophotometric Grade

150. Butyl Alcohol, Natural, >=99.5%, Fcc, Fg

151. C06142

152. D03200

153. Q16391

154. Tributyl Acetylcitrate Impurity D [ep Impurity]

155. F0001-1830

156. Z966690700

157. 1-butanol, Puriss. P.a., Acs Reagent, >=99.5% (gc)

158. Bdbc6468-886d-4f6c-8746-734f2b63e6ce

159. 1-butanol, Acs Reagent, Reag. Iso, Reag. Ph. Eur., 99.5%

160. 1-butanol, United States Pharmacopeia (usp) Reference Standard

161. 1-butanol, Pharmaceutical Secondary Standard; Certified Reference Material

162. 1-butanol, Puriss. P.a., Acs Reagent, Reag. Iso, Reag. Ph. Eur., >=99.5% (gc)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 74.12 g/mol
Molecular Formula C4H10O
XLogP30.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Exact Mass74.073164938 g/mol
Monoisotopic Mass74.073164938 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count5
Formal Charge0
Complexity13.1
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 Minimum/Potential Fatal Human Dose

As extrapolated from rat data ... 3 to 7 oz represents reasonable est of single oral mean lethal dose of any butyl alcohol in man. /Alcohols, higher/

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-13


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Butanol is absorbed through the lung, the GI tract and skin.

Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. Second Edition. Volume 3 Alcohols and Esters. New York, NY: Elsevier, 1992., p. 39


Twelve subjects were exposed to 300 or 600 mg/cu M of n-butyl alcohol in inspired air during rest and during exercise on a bicycle ergometer. Exposure lasted 2 hr. The results were puzzling in view of the high blood/air partition coefficient for butyl alcohol. The arterial blood concentration was low. The concentration in the last part of the expired air, i.e., the ""alveolar'' concentration, was low. The quotient of ""alveolar'' concentration X 100/inspired concentration was low in relation to the low percentage uptake. However the high solubility of butyl alcohol in water may explain the results. Butyl alcohol was probably partially taken up in the water of the dead space mucous membranes during inspiration. It was then partially released from the membranes. Therefore the concentration of butyl alcohol in the last part of expiration was probably not the same as the concentration in the alveolar air.

PMID:973129 Astrand I et al; Scand J Work Environ Health 2 (3): 165-75 (1976)


Volunteers exposed to n-butanol for 2 hr at air concn of 100 and 200 ppm developed blood concn that never exceeded 1.0 mg/L, whether at rest or during excercise. Exposure to an air concn of 50 ppm for 2 hr resulted in blood levels less than 0.08 mg/l.

Baselt, R.C. Biological Monitoring Methods for Industrial Chemicals. 2nd ed. Littleton, MA: PSG Publishing Co., Inc. 1988., p. 51


In rats, n-butanol is extensively metabolized; within 24 hr of a single oral dose, 83% had been converted to carbon dioxide, 4% excreted in the urine and 12% remained in the body.

Baselt, R.C. Biological Monitoring Methods for Industrial Chemicals. 2nd ed. Littleton, MA: PSG Publishing Co., Inc. 1988., p. 51


For more Absorption, Distribution and Excretion (Complete) data for N-BUTYL ALCOHOL (6 total), please visit the HSDB record page.


5.2 Metabolism/Metabolites

Cytochrome p450 isozyme 3a, isolated from hepatic microsomes of rabbits treated chronically with ethyl alcohol, had a unique substrate specificity when compared with isozymes 2, 3b, 3c, and 4. Form 3a has unusually high activity in the p-hydroxylation of aniline and in the oxidation of alcohols to aldehydes. Isozyme 3a catalyzes the oxidation of methyl alcohol, propyl alcohol, and butanol as well as ethyl alcohol.

PMID:7142188 Morgan ET et al; J Biol Chem 257 (23): 13951-7 (1982)


n-Butyl Alcohol may be formed by hydrolysis of butyl acetate in the blood, but is rapidly oxidized.

PMID:18830864 McLain VC. Int J Toxicol. 27 Suppl 2:53-69 (2008).


BA is readily absorbed through the skin, intestinal tract, and lungs and is eliminated after metabolism primarily by alcohol and aldehyde dehydrogenases. ...

OECD; Screening Information Data Set (SIDS) Inital Assessment Report for SIDS Initial Assessment Meeting (SIAM) 13, n-Butyl Alcohol (CAS 71-36-3) p.12 (June 2004). Available from, as of September 25, 2014: https://www.inchem.org/pages/sids.html


In rats, n-butanol is extensively metabolized; within 24 hr of a single oral dose, 83% had been converted to carbon dioxide.

Baselt, R.C. Biological Monitoring Methods for Industrial Chemicals. 2nd ed. Littleton, MA: PSG Publishing Co., Inc. 1988., p. 51


For more Metabolism/Metabolites (Complete) data for N-BUTYL ALCOHOL (6 total), please visit the HSDB record page.


Butanol has known human metabolites that include (2S,3S,4S,5R)-6-Butoxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.3 Mechanism of Action

Alcohols are widely used as industrial solvents and chemical intermediates but can cause serious damage to human health. Nevertheless, few studies have addressed the molecular mechanisms underlying the cytotoxicity of industrial alcohols, with the notable exception of ethanol. The goal of our current study is to elucidate the molecular mechanism of cytotoxicity caused by primary alcohols containing longer carbon chains than ethanol. /The study/ find that 1-butanol induces morphological changes in H9c2 cardiomyoblastoma including nuclear condensation and membrane blebbing, both of which are features of apoptotic response. Moreover, a decrease in the mitochondrial membrane potential, the cytosolic release of cytochrome c, and the activation of caspase 9 and 3 was observed, thus revealing the activation of the mitochondrial apoptotic pathway by 1-butanol. The addition of Y-27632, a specific inhibitor of Rho-associated kinase (ROCK), suppressed the membrane blebbing and mitochondrial apoptotic pathway. In comparison z-VAD-fmk, a pan-caspase inhibitor, did not inhibit membrane blebbing but did prevent cell death following exposure to 1-butanol. These results indicate that mitochondrial pathway of apoptosis and membrane blebbing are parallel phenomena that occur downstream of ROCK. This kinase thus plays an essential role in 1-butanol cytotoxicity and subsequent cell death in H9c2 cells.

PMID:22564901 Noritake K et al; Toxicol In Vitro. 26(6):849-55 (2012).


n-Butanol has been proposed as an alternative biofuel to ethanol, and several industrially used microbes, including Escherichia coli, have been engineered to produce it. Unfortunately, n-butanol is more toxic than ethanol to these organisms. To understand the basis for its toxicity, cell-wide studies were conducted at the transcript, protein, and metabolite levels to obtain a global view of the n-butanol stress response. Analysis of the data indicates that n-butanol stress has components common to other stress responses, including perturbation of respiratory functions (nuo and cyo operons), oxidative stress (sodA, sodC, and yqhD), heat shock and cell envelope stress (rpoE, clpB, htpG, cpxR, and cpxP), and metabolite transport and biosynthesis (malE and opp operon). Assays using fluorescent dyes indicated a large increase in reactive oxygen species during n-butanol stress, confirming observations from the microarray and proteomics measurements. Mutant strains with mutations in several genes whose products changed most dramatically during n-butanol stress were examined for increased sensitivity to n-butanol. Results from these analyses allowed identification of key genes that were recruited to alleviate oxidative stress, protein misfolding, and other causes of growth defects. Cellular engineering based on these cues may assist in developing a high-titer, n-butanol-producing host.

PMID:20118358 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2838030 Rutherford BJ et al; Appl Environ Microbiol. 76(6):1935-45 (2010).


The effects of n-butyl and t-butyl alcohol on the respiration of electrically stimulated and unstimulated slices of rat brain cortical tissue were studied. n-Butyl alcohol, at a concn of 9 mM, and t-butyl alcohol, at a concn of 41 mM, reduced the respiration of stimulated tissue by about 11.5%, and depressed respiration of unstimulated tissue. It is concluded that the alcohols ... act primarily by interfering with mechanisms closely related to the excitation cycle in conducting membranes.

Lindbohm R, Wallgren H; Acta Pharmacol et Toxicol 19 (1): 53-8 (1962)


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31-Mar-2025
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ABOUT THIS PAGE

Looking for 71-36-3 / butanol API manufacturers, exporters & distributors?

butanol manufacturers, exporters & distributors 1

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PharmaCompass offers a list of butanol API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right butanol manufacturer or butanol supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred butanol manufacturer or butanol supplier.

PharmaCompass also assists you with knowing the butanol API Price utilized in the formulation of products. butanol API Price is not always fixed or binding as the butanol Price is obtained through a variety of data sources. The butanol Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

butanol

Synonyms

Butan-1-ol, N-butanol, Butyl alcohol, 71-36-3, N-butyl alcohol, 1-hydroxybutane

Cas Number

71-36-3

Unique Ingredient Identifier (UNII)

8PJ61P6TS3

About butanol

A four carbon linear hydrocarbon that has a hydroxy group at position 1.

butanol Manufacturers

A butanol manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of butanol, including repackagers and relabelers. The FDA regulates butanol manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. butanol API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of butanol manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

butanol Suppliers

A butanol supplier is an individual or a company that provides butanol active pharmaceutical ingredient (API) or butanol finished formulations upon request. The butanol suppliers may include butanol API manufacturers, exporters, distributors and traders.

click here to find a list of butanol suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

butanol KDMF

In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

Pharmaceutical companies submit a butanol Drug Master File in Korea (butanol KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of butanol. The MFDS reviews the butanol KDMF as part of the drug registration process and uses the information provided in the butanol KDMF to evaluate the safety and efficacy of the drug.

After submitting a butanol KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their butanol API can apply through the Korea Drug Master File (KDMF).

click here to find a list of butanol suppliers with KDMF on PharmaCompass.

butanol GMP

butanol Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of butanol GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right butanol GMP manufacturer or butanol GMP API supplier for your needs.

butanol CoA

A butanol CoA (Certificate of Analysis) is a formal document that attests to butanol's compliance with butanol specifications and serves as a tool for batch-level quality control.

butanol CoA mostly includes findings from lab analyses of a specific batch. For each butanol CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

butanol may be tested according to a variety of international standards, such as European Pharmacopoeia (butanol EP), butanol JP (Japanese Pharmacopeia) and the US Pharmacopoeia (butanol USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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