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MedKoo Cat#: 591750 | Name: Monobutyl phthalate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Monobutyl phthalate affects the expressions of EMT-related proteins and enhances the migration and invasion of MLTC-1 cells.

Chemical Structure

Monobutyl phthalate
Monobutyl phthalate
CAS#131-70-4

Theoretical Analysis

MedKoo Cat#: 591750

Name: Monobutyl phthalate

CAS#: 131-70-4

Chemical Formula: C12H14O4

Exact Mass: 222.0892

Molecular Weight: 222.24

Elemental Analysis: C, 64.85; H, 6.35; O, 28.80

Price and Availability

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100g USD 500.00
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Synonym
Monobutyl phthalate; NSC 8479; NSC-8479; NSC8479
IUPAC/Chemical Name
1,2-Benzenedicarboxylic acid, 1-butyl ester
InChi Key
YZBOVSFWWNVKRJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H14O4/c1-2-3-8-16-12(15)10-7-5-4-6-9(10)11(13)14/h4-7H,2-3,8H2,1H3,(H,13,14)
SMILES Code
O=C(C1=CC=CC=C1C(O)=O)OCCCC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Monobutyl phthalate, a major metabolite of dibutyl phthalate (DBP), possesses antiandrogenic effects.
In vitro activity:
This study studied the gene expression profile in embryonic stem cells (ESC) in the early phase of differentiation and its modulation by exposure to the well known embryotoxicant monobutyl phthalate (MBP). Exposure of embryoid bodies (EB) to MBP increased expression of pluripotency-, proliferation- and nonmesodermal differentiation-related gene sets, which indicates inhibition of mesodermal differentiation. Reference: Reprod Toxicol. 2009 Apr;27(2):93-102. https://pubmed.ncbi.nlm.nih.gov/19162170/
In vivo activity:
Similar to MEHP, rats receiving MBP doses starting with 100 mg/kg bw a day had significantly higher liver weight than control, whereas kidney weights did not differ. Absolute pancreas weight significantly decreased in the group treated with the MBP dose of 400 mg/kg bw a day compared to control. This study also noticed a significant decrease in relative pancreas weight in the group receiving the MBP dose of 200 mg/kg bw a day (Table 4). Reference: Arh Hig Rada Toksikol. 2023 Jan 7;73(4):285-296. https://pubmed.ncbi.nlm.nih.gov/36607728/
Solvent mg/mL mM
Solubility
DMSO 72.0 323.97
Ethanol 44.0 197.98
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 222.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Hu Y, Dong C, Chen M, Chen Y, Gu A, Xia Y, Sun H, Li Z, Wang Y. Effects of monobutyl phthalate on steroidogenesis through steroidogenic acute regulatory protein regulated by transcription factors in mouse Leydig tumor cells. J Endocrinol Invest. 2015 Aug;38(8):875-84. doi: 10.1007/s40618-015-0279-6. Epub 2015 Apr 23. PMID: 25903692. 2. van Dartel DA, Pennings JL, Hendriksen PJ, van Schooten FJ, Piersma AH. Early gene expression changes during embryonic stem cell differentiation into cardiomyocytes and their modulation by monobutyl phthalate. Reprod Toxicol. 2009 Apr;27(2):93-102. doi: 10.1016/j.reprotox.2008.12.009. Epub 2008 Dec 31. PMID: 19162170. 3. Karabulut G, Barlas N. Endocrine adverse effects of mono(2-ethylhexyl) phthalate and monobutyl phthalate in male pubertal rats. Arh Hig Rada Toksikol. 2023 Jan 7;73(4):285-296. doi: 10.2478/aiht-2022-73-3617. PMID: 36607728; PMCID: PMC9985344. 4. Zhang Y, Jiao Y, Tao Y, Li Z, Yu H, Han S, Yang Y. Monobutyl phthalate can induce autophagy and metabolic disorders by activating the ire1a-xbp1 pathway in zebrafish liver. J Hazard Mater. 2021 Jun 15;412:125243. doi: 10.1016/j.jhazmat.2021.125243. Epub 2021 Jan 26. PMID: 33524730.
In vitro protocol:
1. Hu Y, Dong C, Chen M, Chen Y, Gu A, Xia Y, Sun H, Li Z, Wang Y. Effects of monobutyl phthalate on steroidogenesis through steroidogenic acute regulatory protein regulated by transcription factors in mouse Leydig tumor cells. J Endocrinol Invest. 2015 Aug;38(8):875-84. doi: 10.1007/s40618-015-0279-6. Epub 2015 Apr 23. PMID: 25903692. 2. van Dartel DA, Pennings JL, Hendriksen PJ, van Schooten FJ, Piersma AH. Early gene expression changes during embryonic stem cell differentiation into cardiomyocytes and their modulation by monobutyl phthalate. Reprod Toxicol. 2009 Apr;27(2):93-102. doi: 10.1016/j.reprotox.2008.12.009. Epub 2008 Dec 31. PMID: 19162170.
In vivo protocol:
1. Karabulut G, Barlas N. Endocrine adverse effects of mono(2-ethylhexyl) phthalate and monobutyl phthalate in male pubertal rats. Arh Hig Rada Toksikol. 2023 Jan 7;73(4):285-296. doi: 10.2478/aiht-2022-73-3617. PMID: 36607728; PMCID: PMC9985344. 2. Zhang Y, Jiao Y, Tao Y, Li Z, Yu H, Han S, Yang Y. Monobutyl phthalate can induce autophagy and metabolic disorders by activating the ire1a-xbp1 pathway in zebrafish liver. J Hazard Mater. 2021 Jun 15;412:125243. doi: 10.1016/j.jhazmat.2021.125243. Epub 2021 Jan 26. PMID: 33524730.
1: Cheng J, Liu Y, Wan Q, Yuan L, Yu X. Degradation of dibutyl phthalate in two contrasting agricultural soils and its long-term effects on soil microbial community. Sci Total Environ. 2018 Jun 4;640-641:821-829. doi: 10.1016/j.scitotenv.2018.05.336. [Epub ahead of print] PubMed PMID: 29879668. 2: Gong P, Lu HC, Zhang C, Chen SS, Wang YB. [Effects of monobutyl phthalate on migration and invasion of mouse Leydig tumor cells]. Zhonghua Yu Fang Yi Xue Za Zhi. 2018 Feb 6;52(2):175-179. doi: 10.3760/cma.j.issn.0253-9624.2018.02.011. Chinese. PubMed PMID: 29429273. 3: Wenzel AG, Brock JW, Cruze L, Newman RB, Unal ER, Wolf BJ, Somerville SE, Kucklick JR. Prevalence and predictors of phthalate exposure in pregnant women in Charleston, SC. Chemosphere. 2018 Feb;193:394-402. doi: 10.1016/j.chemosphere.2017.11.019. Epub 2017 Nov 8. PubMed PMID: 29154114. 4: Huang HB, Chuang CJ, Su PH, Sun CW, Wang CJ, Wu MT, Wang SL. Prenatal and Childhood Exposure to Phthalate Diesters and Thyroid Function in a 9-Year Follow-up Birth Cohort Study: Taiwan Maternal and Infant Cohort Study. Epidemiology. 2017 Oct;28 Suppl 1:S10-S18. doi: 10.1097/EDE.0000000000000722. PubMed PMID: 29028671. 5: Yang P, Gong YJ, Wang YX, Liang XX, Liu Q, Liu C, Chen YJ, Sun L, Lu WQ, Zeng Q. Effect modification by apoptosis-related gene polymorphisms on the associations of phthalate exposure with spermatozoa apoptosis and semen quality. Environ Pollut. 2017 Dec;231(Pt 1):694-702. doi: 10.1016/j.envpol.2017.08.034. Epub 2017 Aug 29. PubMed PMID: 28850937. 6: Kurohane K, Sekiguchi K, Ogawa E, Tsutsumi M, Imai Y. Dibutyl Phthalate Rather than Monobutyl Phthalate Facilitates Contact Hypersensitivity to Fluorescein Isothiocyanate in a Mouse Model. Biol Pharm Bull. 2017 Nov 1;40(11):2010-2013. doi: 10.1248/bpb.b17-00557. Epub 2017 Aug 26. PubMed PMID: 28845027. 7: Saengkaew T, Jantarat C, Nosoognoen W, Supornsilchai V. Association between urinary phthalates and metabolic abnormalities in obese Thai children and adolescents. J Pediatr Endocrinol Metab. 2017 Aug 28;30(9):931-938. doi: 10.1515/jpem-2017-0172. PubMed PMID: 28771440. 8: Gao H, Zhang YW, Huang K, Yan SQ, Mao LJ, Ge X, Xu YQ, Xu YY, Sheng J, Jin ZX, Zhu P, Tao XG, Hao JH, Tao FB. Urinary concentrations of phthalate metabolites in early pregnancy associated with clinical pregnancy loss in Chinese women. Sci Rep. 2017 Jul 28;7(1):6800. doi: 10.1038/s41598-017-06450-2. PubMed PMID: 28754983; PubMed Central PMCID: PMC5533765. 9: Zhang C, Gong P, Ye Y, Zhang L, Chen M, Hu Y, Gu A, Chen S, Wang Y. NF-κB-vimentin is involved in steroidogenesis stimulated by mono-butyl phthalate in primary cultured ovarian granulosa cells. Toxicol In Vitro. 2017 Dec;45(Pt 1):25-30. doi: 10.1016/j.tiv.2017.07.012. Epub 2017 Jul 19. PubMed PMID: 28735033. 10: Moreau M, Leonard J, Phillips KA, Campbell J, Pendse SN, Nicolas C, Phillips M, Yoon M, Tan YM, Smith S, Pudukodu H, Isaacs K, Clewell H. Using exposure prediction tools to link exposure and dosimetry for risk-based decisions: A case study with phthalates. Chemosphere. 2017 Oct;184:1194-1201. doi: 10.1016/j.chemosphere.2017.06.098. Epub 2017 Jun 24. PubMed PMID: 28672700. 11: Kumar V, Sharma N, Maitra SS. Comparative study on the degradation of dibutyl phthalate by two newly isolated Pseudomonas sp. V21b and Comamonas sp. 51F. Biotechnol Rep (Amst). 2017 Apr 28;15:1-10. doi: 10.1016/j.btre.2017.04.002. eCollection 2017 Sep. PubMed PMID: 28580302; PubMed Central PMCID: PMC5447571. 12: Sugino M, Hatanaka T, Todo H, Mashimo Y, Suzuki T, Kobayashi M, Hosoya O, Jinno H, Juni K, Sugibayashi K. Safety evaluation of dermal exposure to phthalates: Metabolism-dependent percutaneous absorption. Toxicol Appl Pharmacol. 2017 Aug 1;328:10-17. doi: 10.1016/j.taap.2017.05.009. Epub 2017 May 12. PubMed PMID: 28506834. 13: Du J, Xiong D, Zhang Q, Li X, Liu X, You H, Ding S, Yang X, Yuan J. Mono-butyl phthalate-induced mouse testis injury is associated with oxidative stress and down-regulated expression of Sox9 and Dazl. J Toxicol Sci. 2017;42(3):319-328. doi: 10.2131/jts.42.319. PubMed PMID: 28496037. 14: Gao H, Zhu YD, Xu YY, Zhang YW, Yao HY, Sheng J, Jin ZX, Ren LL, Huang K, Hao JH, Tao FB. Season-dependent concentrations of urinary phthalate metabolites among Chinese pregnant women: Repeated measures analysis. Environ Int. 2017 Jul;104:110-117. doi: 10.1016/j.envint.2017.03.021. Epub 2017 Apr 4. PubMed PMID: 28389128. 15: Wang IJ, Karmaus WJ. Oxidative Stress-Related Genetic Variants May Modify Associations of Phthalate Exposures with Asthma. Int J Environ Res Public Health. 2017 Feb 8;14(2). pii: E162. doi: 10.3390/ijerph14020162. PubMed PMID: 28208751; PubMed Central PMCID: PMC5334716. 16: Thomsen AM, Riis AH, Olsen J, Jönsson BA, Lindh CH, Hjollund NH, Jensen TK, Bonde JP, Toft G. Female exposure to phthalates and time to pregnancy: a first pregnancy planner study. Hum Reprod. 2017 Jan;32(1):232-238. Epub 2016 Nov 16. PubMed PMID: 27852689. 17: Lin Q, Chen S, Chao Y, Huang X, Wang S, Qiu R. Carboxylesterase-involved metabolism of di-n-butyl phthalate in pumpkin (Cucurbita moschata) seedlings. Environ Pollut. 2017 Jan;220(Pt A):421-430. doi: 10.1016/j.envpol.2016.09.084. Epub 2016 Sep 30. PubMed PMID: 27697378. 18: Corbasson I, Hankinson SE, Stanek EJ 3rd, Reeves KW. Urinary bisphenol-A, phthalate metabolites and body composition in US adults, NHANES 1999-2006. Int J Environ Health Res. 2016 Oct-Dec;26(5-6):606-17. doi: 10.1080/09603123.2016.1233524. Epub 2016 Sep 19. PubMed PMID: 27643383. 19: Hu X, Gu Y, Huang W, Yin D. Phthalate monoesters as markers of phthalate contamination in wild marine organisms. Environ Pollut. 2016 Nov;218:410-418. doi: 10.1016/j.envpol.2016.07.020. Epub 2016 Jul 18. PubMed PMID: 27435611. 20: Wallner P, Kundi M, Hohenblum P, Scharf S, Hutter HP. Phthalate Metabolites, Consumer Habits and Health Effects. Int J Environ Res Public Health. 2016 Jul 15;13(7). pii: E717. doi: 10.3390/ijerph13070717. PubMed PMID: 27428989; PubMed Central PMCID: PMC4962258.

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CP-85958

CP-85958