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CAS 85-68-7 manufacturers and suppliers on PharmaCompass

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

benzyl butyl phthalate is a natural product found in Scolochloa festucacea, Lolium arundinaceum, and Festuca rubra with data available.
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. Santicizer 160

6. Butylbenzyl Phthalate

7. Unimoll Bb

8. Benzyl N-butyl Phthalate

9. N-butyl Benzyl Phthalate

10. Sicol 160

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

12. Butylbenzylphthalate

13. Phthalic Acid, Benzyl Butyl Ester

14. Bbp

15. Phthalic Acid Benzyl Butyl Ester

16. Nci-c54375

17. 2-o-benzyl 1-o-butyl Benzene-1,2-dicarboxylate

18. Nsc 71001

19. Butyl Phenylmethyl 1,2-benzenedicarboxylate

20. Benzyl-butylester Kyseliny Ftalove

21. Ypc4pjx59m

22. Benzyl Butyl Benzene-1,2-dicarboxylate

23. Dtxsid3020205

24. 1,2-benzenedicarboxylic Acid, 1-butyl 2-(phenylmethyl) Ester

25. Chebi:34595

26. Nsc-71001

27. Ncgc00090780-04

28. Dsstox_cid_205

29. Dsstox_rid_75431

30. Dsstox_gsid_20205

31. Benzyl Butylphthalate

32. Phthalic Acid, Benzylbutyl Ester

33. Caswell No. 125g

34. Cas-85-68-7

35. Ketjenflex 160

36. Ccris 104

37. Benzyl Butyl Phthalate, Analytical Standard

38. Diacizer D 160

39. Santicizer S 160

40. Hsdb 2107

41. Einecs 201-622-7

42. Unii-ypc4pjx59m

43. Brn 2062204

44. Benzyl-butylester Kyseliny Ftalove [czech]

45. Ai3-14777

46. Benzylbutylphthalate

47. Mfcd00009440

48. Benzyl-butyl-phthalate

49. Benzyl Butyl Phthalated

50. Spectrum_001977

51. 4mg6

52. Benyl N-butyl Phthalate

53. Butyl Phenylmethyl Ester

54. Specplus_000622

55. Spectrum2_001805

56. Spectrum3_000871

57. Spectrum4_000711

58. Spectrum5_002070

59. Wln: Qvr Bvo1r

60. Phthalic Acid Benzyl Butyl

61. Ec 201-622-7

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

63. 1, Butyl Phenylmethyl Ester

64. Bbp, Benzyl Butyl Phthalate

65. Schembl49678

66. Bspbio_002541

67. Kbiogr_001261

68. Kbioss_002543

69. Mls002177799

70. Benzyl Butyl Phthalate, 98%

71. Bidd:er0643

72. Divk1c_006718

73. Spbio_001789

74. 1-benzyl 2-butyl Phthalate #

75. Chembl1450327

76. Kbio1_001662

77. Kbio2_002534

78. Kbio2_005102

79. Kbio2_007670

80. Kbio3_002041

81. Hms3039o09

82. Phthalic Acid Benzyl N-butyl Ester

83. Nsc71001

84. Zinc1696593

85. Tox21_202991

86. Tox21_400057

87. Ccg-39615

88. S5822

89. Butyl Benzyl Phthalate [hsdb]

90. Butyl Benzyl Phthalate [iarc]

91. Butyl Benzyl Phthalate [inci]

92. Akos015839717

93. Phthalic Acid Benzyl Ester Butyl Ester

94. Cs-w012054

95. Hy-w011338

96. Ncgc00090780-01

97. Ncgc00090780-02

98. Ncgc00090780-03

99. Ncgc00090780-05

100. Ncgc00260536-01

101. Smr001261796

102. 1-benzyl 2-butyl Benzene-1,2-dicarboxylate

103. Ft-0655622

104. Ft-0662711

105. P0288

106. Q414809

107. Q-101286

108. Brd-k34359596-001-02-1

109. Phthalic Acid, Benzylbutyl Ester 100 Microg/ml In Acetonitrile

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

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

112. 27g

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 312.4 g/mol
Molecular Formula C19H20O4
XLogP34.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Exact Mass312.13615911 g/mol
Monoisotopic Mass312.13615911 g/mol
Topological Polar Surface Area52.6 Ų
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.

PMID:2925020 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. ...

PMID:3959124 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: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 119 (1999)


For more Absorption, Distribution and Excretion (Complete) data for BUTYL BENZYL PHTHALATE (8 total), please visit the HSDB record page.


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). ...

PMID:3959124 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...

PMID:14998749 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/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. ...

PMID:11761117 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. ...

PMID:10506015 Nativelle C et al; Food Chem Toxicol 37 (8): 905-17 (1999)


For more Metabolism/Metabolites (Complete) data for BUTYL BENZYL PHTHALATE (9 total), please visit the HSDB record page.


4.4 Biological Half-Life

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.

PMID:3959124 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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