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Overview of CAS 85-68-7

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4mg6
PharmaCompass
  • Chemistry
4mg6
Also known as: Butyl benzyl phthalate, 85-68-7, Sicol, Palatinol bb, Unimoll bb, Santicizer 160
Molecular Formula
C19H20O4
Molecular Weight
312.365  g/mol
InChI Key
IRIAEXORFWYRCZ-UHFFFAOYSA-N
FDA UNII
YPC4PJX59M

1 2D Structure

4mg6

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-O-benzyl 1-O-butyl benzene-1,2-dicarboxylate
2.1.2 InChI
InChI=1S/C19H20O4/c1-2-3-13-22-18(20)16-11-7-8-12-17(16)19(21)23-14-15-9-5-4-6-10-15/h4-12H,2-3,13-14H2,1H3
2.1.3 InChI Key
IRIAEXORFWYRCZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCOC(=O)C1=CC=CC=C1C(=O)OCC2=CC=CC=C2
2.2 Other Identifiers
2.2.1 UNII
YPC4PJX59M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bbpht

2. Butyl Benzyl Phthalate

3. Butylbenzyl Phthalate

2.3.2 Depositor-Supplied Synonyms

1. Butyl Benzyl Phthalate

2. 85-68-7

3. Sicol

4. Palatinol Bb

5. Unimoll Bb

6. Santicizer 160

7. Butylbenzyl Phthalate

8. N-butyl Benzyl Phthalate

9. Sicol 160

10. Benzyl N-butyl Phthalate

11. 1,2-benzenedicarboxylic Acid, Butyl Phenylmethyl Ester

12. Butylbenzylphthalate

13. Phthalic Acid Benzyl Butyl Ester

14. Phthalic Acid, Benzyl Butyl Ester

15. Benzyl Butylphthalate

16. Nci-c54375

17. Nsc 71001

18. Caswell No. 125g

19. Spatozoate

20. Bbp

21. Unii-ypc4pjx59m

22. Butyl Phenylmethyl 1,2-benzenedicarboxylate

23. Ccris 104

24. Santicizer S 160

25. Hsdb 2107

26. Benzyl-butylester Kyseliny Ftalove

27. Einecs 201-622-7

28. Mfcd00009440

29. Ypc4pjx59m

30. Brn 2062204

31. Benzyl-butylester Kyseliny Ftalove [czech]

32. Ai3-14777

33. Chebi:34595

34. Iriaexorfwyrcz-uhfffaoysa-n

35. Phthalic Acid Benzyl N-butyl Ester

36. Benzyl Butyl Benzene-1,2-dicarboxylate

37. Ncgc00090780-04

38. Ak114582

39. 1,2-benzenedicarboxylic Acid, 1-butyl 2-(phenylmethyl) Ester

40. Dsstox_cid_205

41. O2-benzyl O1-butyl Benzene-1,2-dicarboxylate

42. Dsstox_rid_75431

43. 2-o-benzyl 1-o-butyl Benzene-1,2-dicarboxylate

44. Dsstox_gsid_20205

45. Q-101286

46. Phenylmethyl 2-(butoxycarbonyl)benzoate

47. Cas-85-68-7

48. Benzyl Butyl Phthalate, Analytical Standard

49. Benzylbutylphthalate

50. Ketjenflex 160

51. Santi Cizer 160

52. Santicizer C 160

53. Santicizer S 106

54. Diacizer D 160

55. Benzyl-butyl-phthalate

56. Butyl-benzyl-phthalate

57. Benzyl Butyl Phthalated

58. Spectrum_001977

59. 4mg6

60. Benyl N-butyl Phthalate

61. Butyl Phenylmethyl Ester

62. Specplus_000622

63. Ac1q2xao

64. Sant 160

65. Spectrum2_001805

66. Spectrum3_000871

67. Spectrum4_000711

68. Spectrum5_002070

69. Wln: Qvr Bvo1r

70. Phthalic Acid Benzyl Butyl

71. Acmc-209q7a

72. Ec 201-622-7

73. Ac1l1dh6

74. 1, Butyl Phenylmethyl Ester

75. Bbp, Benzyl Butyl Phthalate

76. Schembl49678

77. Bspbio_002541

78. Kbiogr_001261

79. Kbioss_002543

80. Mls002177799

81. Benzyl Butyl Phthalate, 98%

82. Bidd:er0643

83. Divk1c_006718

84. Spbio_001789

85. 1-benzyl 2-butyl Phthalate #

86. Chembl1450327

87. Dtxsid3020205

88. Phthalic Acid, Benzylbutyl Ester

89. Ctk3e8736

90. Kbio1_001662

91. Kbio2_002534

92. Kbio2_005102

93. Kbio2_007670

94. Kbio3_002041

95. N-butyl Benzyl Phthalate Diester

96. Hms3039o09

97. Ks-000011gs

98. Nsc71001

99. Zinc1696593

100. Tox21_202991

101. Tox21_400057

102. Anw-38228

103. Ccg-39615

104. Nsc-71001

105. Sbb061464

106. Akos015839717

107. Ls-1849

108. Mcule-4779280535

109. Rtr-031858

110. Ncgc00090780-01

111. Ncgc00090780-02

112. Ncgc00090780-03

113. Ncgc00090780-05

114. Ncgc00260536-01

115. Aj-30310

116. An-42322

117. M133

118. Sc-18153

119. Smr001261796

120. Ax8119127

121. Tr-031858

122. 1-benzyl 2-butyl Benzene-1,2-dicarboxylate

123. Ft-0655622

124. P0288

125. S 160

126. St24030153

127. St50319877

128. C14211

129. I06-1649

130. 1,2-benzenedicarboxylic Acid Butyl Phenylmethyl Ester

131. Brd-k34359596-001-02-1

132. 1,2-benzenedicarboxylic Acid 1-butyl 2-(phenylmethyl) Ester

133. Phthalic Acid, Benzylbutyl Ester 1000 Microg/ml In Cyclohexane

134. Benzyl Butyl Phthalate, Certified Reference Material, Tracecert(r)

135. 27g

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 312.365 g/mol
Molecular Formula C19H20O4
XLogP34.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Exact Mass312.136 g/mol
Monoisotopic Mass312.136 g/mol
Topological Polar Surface Area52.6 A^2
Heavy Atom Count23
Formal Charge0
Complexity374
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Teratogens

An agent that causes the production of physical defects in the developing embryo. (See all compounds classified as Teratogens.)


4.2 Absorption, Distribution and Excretion

This study examined the extent of dermal absorption of a series of phthalate diesters in the rat. Those tested were dimethyl, diethyl, dibutyl, diisobutyl, dihexyl, di(2-ethylhexyl), diisodecyl, and benzyl butyl phthalate. Hair from a skin area (1.3 cm in diameter) on the back of male F344 rats was clipped, the 14C-phthalate diester was applied in a dose of 157 umol/kg, and the area of application was covered with a perforated cap. The rat was restrained and housed for 7 days in a metabolic cage that allowed separate collection of urine and feces. Urine and feces were collected every 24 hr, and the amount of carbon-14 excreted was taken as an index of the percutaneous absorption. At 24 hr, diethyl phthalate showed the greatest excretion (26%). As the length of the alkyl side chain increased, the amount of carbon-14 excreted in the first 24 hr decreased significantly. The cumulative percentage dose excreted in 7 days was greatest for diethyl, dibutyl, and diisobutyl phthalate, about 50-60% of the applied 14C; and intermediate (20-40%) for dimethyl, benzyl butyl, and dihexyl phthalate. Urine was the major route of excretion of all phthalate diesters except for diisodecyl phthalate. This compound was poorly absorbed and showed almost no urinary excretion. After 7 days, the percentage dose for each phthalate that remained in the body was minimal and showed no specific tissue distribution. Most of the unexcreted dose remained in the area of application. These data show that the structure of the phthalate diester determines the degree of dermal absorption. Absorption maximized with diethyl phthalate and then decreased significantly as the alkyl side chain length increased. PubMed Abstract

Elsisi AE et al; Fundam Appl Toxicol 12(1): 70-7 (1989)


... Male Fischer-344 rats were dosed with (14)C-labeled butyl benzyl phthalate (BBP) at 2, 20, 200, or 2000 mg/kg orally or 20 mg/kg iv to detect the effects of dose on rates and routes of excretion. In 24 hr, 61-74% of the dose was excreted in the urine and 13-19% in the feces at 2-200 mg/kg. At 2000-mg/kg, 16% of the (14)C was excreted in the urine and 57% in the feces. Urinary (14)C was composed of monophthalate glucuronides derivatives (MP: 10-42% of the dose) and monophthalate glucuronides (2-21% of the dose). At 4 hr after iv administration of BBP (20 mg/kg), 53-58% of the dose was excreted in the bile of anesthetized rats. BBP was not found in the bile, but monobutyl glucuronide and monobenzyl phthalate glucuronide (26 and 13% of the dose, respectively) and trace amts of free monoesters (2% of the dose) and unidentified metabolites (14% of the dose) were present. ... The half-lives of BBP, MP, and total (14)C in blood (20 mg/kg, iv) were 10 min, 5.9 hr, and 6.3 hr, respectively. ... PubMed Abstract

Eigenberg DA et al; J Toxicol Environ Health 17 (4): 445-56 (1986)


Following intravenous administration of 20 mg/kg of (14)C-BBP, 55% of the dose was excreted into bile and 34% was excreted into the urine.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6 869


Beagle dogs were given a 5 g/kg bw oral dose of butyl benzyl phthalate divided over a 4 hr period. Unchanged butyl benzyl phthalate in the feces comprised 88-91% of the dose. While butyl benzyl phthalate was not present in the urine, some 4.2% of the dose was present as phthalic acid

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarc.fr/ENG/Classification/index.php, p. V73 119 (1999)


Male Fischer 344 rats received a single dermal application of 30-40 mg/kg (5-8 mg/sq cm) of 14C-BBP on their backs. The BBP was applied in ethanol. 'The site was clipped of hair prior to application and covered with a perforated cap after treatment. The rats were restrained and housed for 7 days in metabolic cages to collect urine and feces. About 30% of the dose was excreted in the urine and feces within 7 days. About 45% of the dose remained at the application site.

European Chemicals Bureau; IUCLID Dataset, Benzyl butyl phthalate (85-68-7) p. 32 (2000 CD-ROM edition). Available from, as of April 28, 2008: http://esis.jrc.ec.europa.eu/


After dermal application of 157 umol/kg bw (about 49 mg/kg bw) (ring-(14)C)butyl benzyl phthalate to the shaved skin of male Fischer 344 rats, some 30% of the dose was excreted in the urine and feces within seven days; 45% of the dose was found in the skin at the application site, 6.3% in the plastic cap used to occlude the skin and 4.6% in muscle and <1% in other tissues.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarc.fr/ENG/Classification/index.php, p. V73 119 (1999)


In a recent study... , it was shown that people efficiently absorb ... and excrete BBP. Volunteers given an oral dose of BBP excrete approximately 75% of the dose in urine within 24 hours. ...

DHHS/NTP-CERHR Monograph on the Potential Human Reproductive and Developmental Effects of Butyl Benzyl Phthalate (BBP) p. 1 (2003) NIH Publication No. 03-4487


Administration of single oral doses of 2, 20, 200, or 2,000 mg/kg to male Fischer 344 rats showed a dose-dependent increase in the fraction of dose eliminated via the feces (20% at doses from 2-200 mg/kg; 72% at 2,000 mg/kg) and a dose-dependent decrease in the fraction eliminated via the urine (75% at a dose of 2-200 mg/kg and 22% at 2,000 mg/kg), suggesting that absorption through the gut was limited at the high dose.

DHHS/NTP-CERHR Monograph on the Potential Human Reproductive and Developmental Effects of Butyl Benzyl Phthalate (BBP) p. 23 (2003) NIH Publication No. 03-4487


4.3 Metabolism/Metabolites

BBP was not found in the bile, but monobutyl glucuronide and monobenzyl phthalate glucuronide (26 and 13% of the dose, respectively) and trace amounts of free monoesters (2% of the dose) and unidentified metabolites (14% of the dose) were present. Although BBP is an asymetrical diester with the potential of forming equal amounts of monobutyl phthalate and monobenzyl phthalate, larger quantities of monobutyl phthalate were formed (monobutyl phthalate= 44% vs monobenzyl phthalate= 16% of the dose). ... PubMed Abstract

Eigenberg DA et al; J Toxicol Environ Health 17 (4): 445-56 (1986)


The urinary monoester metabolites of seven commonly used phthalates /were measured/ in approximately 2,540 samples collected from participants of the National Health and Nutrition Examination Survey (NHANES), 1999-2000, who were greater than or equal to 6 years of age. ... Detectable levels of metabolites monoethyl phthalate (MEP), monobutyl phthalate (MBP), monobenzyl phthalate (MBzP), and mono-(2-ethylhexyl) phthalate (MEHP) /were found/ in > 75% of the samples, suggesting widespread exposure in the United States to diethyl phthalate, dibutyl phthalate or diisobutylphthalate, benzylbutyl phthalate, and di-(2-ethylhexyl) phthalate, respectively. ... Monoisononyl phthalate, mono-cyclohexyl phthalate, and mono-n-octyl phthalate /were detected infrequently/, suggesting that human exposures to di-isononyl phthalate, dioctylphthalate, and dicyclohexyl phthalate, respectively, are lower than those listed above, or the pathways, routes of exposure, or pharmacokinetic factors such as absorption, distribution, metabolism, and elimination are different. Non-Hispanic blacks had significantly higher concentrations of MEP than did Mexican Americans and non-Hispanic whites. Compared with adolescents and adults, children had significantly higher levels of MBP, MBzP, and MEHP but had significantly lower concentrations of MEP. Females had significantly higher concentrations of MEP and MBzP than did males, but similar MEHP levels. Of particular interest, females of all ages had significantly higher concentrations of the reproductive toxicant MBP than did males of all ages; however, women of reproductive age (i.e., 20-39 years of age) had concentrations similar to adolescent girls and women 40 years of age... PubMed Abstract Full text: PMC1241863

Silva MJ et al; Environ Health Perspect 112 (3): 331-8 (2004); Erratum in: Environ Health Perspect 112 (5): A270 (2004).


Three groups of eight volunteers were administered stable isotope-labelled ... benzylbutylphthalate. ... For benzylbutylphthalate, 67% and 78% was eliminated as monobenzylphthalate and only 6% (measured for the high dose only) was eliminated as monobutylphthalate. ... PubMed Abstract

Anderson WA et al; Food Addit Contam 18 (12): 1068-74 (2001)


n-Butyl benzyl phthalate (BBP) ... has been orally administered to female Wistar rats with four doses (150, 475, 780 and 1500 mg/kg body weight/day) for 3 consecutive days. Metabolites recovered in urine were analyzed by gas chromatography-mass spectrometry (GC-MS) after 24, 48 and 72 hours. Six metabolites were identified. Mono-n-butyl phthalate (MBuP) and mono-n-benzyl phthalate (MBeP) represented respectively 29-34% and 7-12% of the total recovered metabolites. Hippuric acid, the main metabolite of benzoic acid, represented the second major metabolite (51-56%). Phthalic acid, benzoic acid and an omega-oxidized metabolite of MBuP were also recovered in urine but in small quantities. BBP was never identified in urine. Total urinary metabolites recovery represented 56% of the dose administered in the first 24 hours. However, total recovery decreased when the dose increases (43% at 780 mg/kg body weight/day, only 30% at 1500 mg/kg body weight/day). Whatever the time was, BBP metabolites recovered in urine were all present and in the same proportions for the two lowest doses. Discrepancy in metabolites quantities expressed as percentages of the dose observed in urine of rat treated with the highest BBP dose disappeared with time as MBuP, MBeP and hippuric acid recovery has significantly increased at day 3. ... PubMed Abstract

Nativelle C et al; Food Chem Toxicol 37 (8): 905-17 (1999)


... Monoester metabolites of seven commonly used phthalates in urine samples /were measured/ from a reference population of 289 adult humans. ... The monoesters with the highest urinary levels found were monoethyl phthalate (95th percentile, 3,750 ppb, 2,610 ug/g creatinine), monobutyl phthalate (95th percentile, 294 ppb, 162 ug/g creatinine), and monobenzyl phthalate (95th percentile, 137 ppb, 92 ug/g creatinine), reflecting exposure to diethyl phthalate, dibutyl phthalate, and benzyl butyl phthalate. Women of reproductive age (20-40 years) were found to have significantly higher levels of monobutyl phthalate, a reproductive and developmental toxicant in rodents, than other age/gender groups (p < 0.005). ... /These /findings strongly suggest that health-risk assessments for phthalate exposure in humans should include diethyl, dibutyl, and benzyl butyl phthalates. PubMed Abstract Full text: PMC1240132

Blount BC et al; Environ Health Perspect 108 (10): 979-82 (2000); Comments in Environ Health Perspect 108(10):A440 (2000) and Environ Health Perspect 108 (10):A440-2 (2000)


Examination of urinary metabolites of rats following oral administration of 3.6 mmol BBP/kg/day for 3 days indicated that approximately 70% of the metabolites were unconjugated monoesters, while the remainder was conjugated. A dose-dependent change in both the route of excretion and the ratio of certain metabolites was observed, with urinary excretion predominating at lower doses and fecal excretion observed at higher doses. It can be concluded that BBP is rapidly metabolized to monoester components. These components are either excreted directly or are conjugated and excreted.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6 869


In a recent study ..., it was shown that people efficiently ... metabolize ... BBP. ... Most of the dose is excreted as the mono-benzyl phthalate metabolite, with only a minor fraction excreted as the mono-butyl phthalate.

DHHS/NTP-CERHR Monograph on the Potential Human Reproductive and Developmental Effects of Butyl Benzyl Phthalate (BBP) p. 1 (2003) NIH Publication No. 03-4487


People exposed to BzBP will excrete mono-benzyl phthalate (MBzP) and small amounts of mono-n-butyl phthalate in their urine. High dose BzBP and its monoester metabolites, including MBzP, can produce developmental and reproductive toxicity in rodents, particularly male animals...

CDC; Fourth National Report on Human Exposure to Environmental Benzylbutyl Phthalate CAS No. 85-68-7, p. 262 (2009); Available from, as of March 10, 2015: http://www.cdc.gov/exposurereport


Human biomonitoring studies measuring phthalate metabolites in urine have shown widespread exposure to phthalates in the general population. Diet is thought to be a principle route of exposure to many phthalates. Therefore, we studied urinary phthalate metabolite patterns over a period of strict fasting and additionally recorded personal activity patterns with a diary to investigate non-dietary routes of exposure. Five individuals (3 female, 2 male, 27-47 years of age) fasted on glass-bottled water only over a 48-h period. All urine void events were captured in full, and measured for metabolites of the high molecular weight (HMW) di-(2-ethylhexyl) phthalate (DEHP), di-isononyl phthalate (DINP) and di-isodecyl phthalate (DiDP), and the low molecular weight (LMW) di-n-butyl phthalate (DnBP), di-iso-butyl phthalate (DiBP), butylbenzyl phthalate (BBzP), dimethyl phthalate (DMP), and diethyl phthalate (DEP). In all, 21 metabolites were measured in a total of 118 urine events, including events before and after the fasting period. At the onset of the study all phthalate metabolite concentrations were consistent with levels found in previous general population studies. Metabolites of the HMW phthalates (DEHP, DiNP and DiDP) showed a rapid decline to levels 5-10 times lower than initial levels within 24hr of the fast and remained low thereafter. After food consumption resumed, levels rose again. By contrast, metabolites of the LMW phthalates including DMP, DEP, BBzP, DnBP and DiBP showed a cyclical pattern of rising and declining concentrations suggestive of ongoing non-food exposures. Furthermore, metabolites of most of the LMW phthalates (BBzP, DnBP and DiBP) tracked each other remarkably well, suggesting concurrent exposures. Diary entries could not help explain exposure sources for these phthalates, with one exception: rises in MEP concentrations around males' showers suggest personal care products as a major source of DEP. Exposure to HMW phthalates in this cohort appears to be driven by dietary intake, while non-dietary routes such as use of personal care products and ubiquitous sources including dust and indoor air appear to explain exposure to LMW phthalates. PubMed Abstract

Koch HM et al; Int J Hyg Environ Health. 216 (6): 672-81 (2013)


4.4 Biological Half-Life

Fish Biotrans. Half-Life (Km)

0.09 Days


The half-lives of butyl benzyl phthalate (BBP), monophthalate (MP), and total (14)C in blood (20 ng/kg, intravenously) were 10 min, 5.9 hr, and 6.3 hr, respectively. PubMed Abstract

Eigenberg DA et al; J Toxicol Environ Health 17 (4): 445-56 (1986)


The half-life of BBP in blood is 10 min following an oral administration of 5 g/kg to dogs.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6 869


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