Phthalic acid | CAS#88-99-3 | aromatic dicarboxylic acid

MedKoo Cat#: 591779 | Name: Phthalic acid

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Description:

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

Phthalic acid is an aromatic dicarboxylic acid, with formula C₆H₄(CO₂H)₂. It is an isomer of isophthalic acid and terephthalic acid.

Chemical Structure

Phthalic acid

CAS#88-99-3

Theoretical Analysis

MedKoo Cat#: 591779

Name: Phthalic acid

CAS#: 88-99-3

Chemical Formula: C8H6O4

Exact Mass: 166.0266

Molecular Weight: 166.13

Elemental Analysis: C, 57.84; H, 3.64; O, 38.52

Price and Availability

Size	Price	Availability	Quantity
25g	USD 220.00
500g	USD 370.00

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Related CAS #

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Synonym

Phthalic acid; NSC 5348; NSC-5348; NSC5348

IUPAC/Chemical Name

1,2-Benzenedicarboxylic acid

InChi Key

XNGIFLGASWRNHJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)

SMILES Code

O=C(C1=CC=CC=C1C(O)=O)O

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:

Phthalic acid is the final common metabolite of phthalic acid esters (PAEs).

In vitro activity:

This study investigated the effects of DEHP, DBP, and their mixture on rat insulinoma (INS-1) cell apoptosis and the mechanism involved in vitro. This study was the first to show that the combined effect of the two PAEs (phthalic acid esters) promotes a ROS-mediated PI3K/Akt/Bcl-2 pathway-induced pancreatic β cell apoptosis that is significantly higher than the effects of each PAE. Reference: Ecotoxicol Environ Saf. 2021 Jan 15;208:111461. https://pubmed.ncbi.nlm.nih.gov/33091774/

In vivo activity:

The current study aimed to investigate the effects of prenatal PA (phthalic acid) exposure on the markers of oxidative stress and cardiac structure in rats' offspring. By a dose-dependent manner, the body weight (BW), heart weight (HW), and HW/BW of the intervention groups were reduced and their heart rate and blood pressure were conversely increased compared to the control group. Also, the wall thickness, cross-sectional area of the aorta and septal branch of the descending left coronary artery were significantly increased in the intervention group. In addition, PA significantly increased the level of malondialdehyde and decreased the level of superoxide dismutase and glutathione peroxidase, compared to the control group. This study revealed that prenatal exposure of rats to PA causes vascular dysfunction, increasing oxidative stress, and reduction in cardiac nitric oxide synthetase activity among offspring rats. Reference: Cardiovasc Toxicol. 2016 Oct;16(4):307-15. https://pubmed.ncbi.nlm.nih.gov/26293546/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	601.93

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 166.13 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.

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. Cosci I, Garolla A, Cabrelle A, Sut S, Dall'Acqua S, Ferlin A, Foresta C, De Toni L. Lipophilic phthalic acid esters impair human sperm acrosomal reaction through the likely inhibition of phospholipase A2-signaling pathway. Biochem Pharmacol. 2022 Nov;205:115249. doi: 10.1016/j.bcp.2022.115249. Epub 2022 Sep 15. PMID: 36115423. 2. Li L, Wang F, Zhang J, Wang K, De X, Li L, Zhang Y. Typical phthalic acid esters induce apoptosis by regulating the PI3K/Akt/Bcl-2 signaling pathway in rat insulinoma cells. Ecotoxicol Environ Saf. 2021 Jan 15;208:111461. doi: 10.1016/j.ecoenv.2020.111461. Epub 2020 Oct 19. PMID: 33091774. 3. Rahmani A, Soleimannejad K, Hafezi Ahmadi MR, Asadollahi K, Khalighi Z. Prenatal Exposure to Phthalic Acid Induces Increased Blood Pressure, Oxidative Stress, and Markers of Endothelial Dysfunction in Rat Offspring. Cardiovasc Toxicol. 2016 Oct;16(4):307-15. doi: 10.1007/s12012-015-9337-8. PMID: 26293546. 4. Oishi S. Effects of phthalic acid esters on testicular mitochondrial functions in the rat. Arch Toxicol. 1990;64(2):143-7. doi: 10.1007/BF01974400. PMID: 2350233.

In vitro protocol:

In vivo protocol:

1. Rahmani A, Soleimannejad K, Hafezi Ahmadi MR, Asadollahi K, Khalighi Z. Prenatal Exposure to Phthalic Acid Induces Increased Blood Pressure, Oxidative Stress, and Markers of Endothelial Dysfunction in Rat Offspring. Cardiovasc Toxicol. 2016 Oct;16(4):307-15. doi: 10.1007/s12012-015-9337-8. PMID: 26293546. 2. Oishi S. Effects of phthalic acid esters on testicular mitochondrial functions in the rat. Arch Toxicol. 1990;64(2):143-7. doi: 10.1007/BF01974400. PMID: 2350233.

1: Chen N, Fang G, Liu G, Zhou D, Gao J, Gu C. The effects of Fe-bearing smectite clays on OH formation and diethyl phthalate degradation with polyphenols and H(2)O(2). J Hazard Mater. 2018 Jun 21;357:483-490. doi: 10.1016/j.jhazmat.2018.06.030. [Epub ahead of print] PubMed PMID: 29936346. 2: Santana-Mayor Á, Socas-Rodríguez B, Afonso MDM, Palenzuela-López JA, Rodríguez-Delgado MÁ. Reduced graphene oxide-coated magnetic-nanoparticles as sorbent for the determination of phthalates in environmental samples by micro-dispersive solid-phase extraction followed by ultra-high-performance liquid chromatography tandem mass spectrometry. J Chromatogr A. 2018 Jun 13. pii: S0021-9673(18)30773-8. doi: 10.1016/j.chroma.2018.06.031. [Epub ahead of print] PubMed PMID: 29935815. 3: Wang T, Qu G, Yin X, Sun Q, Liang D, Guo X, Jia H. Dimethyl phthalate elimination from micro-polluted source water by surface discharge plasma: Performance, active species roles and mechanisms. J Hazard Mater. 2018 Jun 5;357:279-288. doi: 10.1016/j.jhazmat.2018.06.014. [Epub ahead of print] PubMed PMID: 29894928. 4: Guevara-Luna J, Alvarez-Fitz P, Ríos-Leal E, Acevedo-Quiroz M, Encarnación-Guevara S, Moreno-Godinez ME, Castellanos-Escamilla M, Toribio-Jiménez J, Romero-Ramírez Y. Biotransformation of benzo[a]pyrene by the thermophilic bacterium Bacillus licheniformis M2-7. World J Microbiol Biotechnol. 2018 Jun 9;34(7):88. doi: 10.1007/s11274-018-2469-9. PubMed PMID: 29886516. 5: 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. 6: Lu X, Xu X, Lin Y, Zhang Y, Huo X. Phthalate exposure as a risk factor for hypertension. Environ Sci Pollut Res Int. 2018 Jun 3. doi: 10.1007/s11356-018-2367-6. [Epub ahead of print] PubMed PMID: 29862479. 7: Zhang S, Yang Q, Li Z, Wang W, Zang X, Wang C, Wang Z. Solid phase microextraction of phthalic acid esters from vegetable oils using iron (III)-based metal-organic framework/graphene oxide coating. Food Chem. 2018 Oct 15;263:258-264. doi: 10.1016/j.foodchem.2018.04.132. Epub 2018 Apr 30. PubMed PMID: 29784315. 8: Fan S, Wang J, Li K, Yang T, Jia Y, Zhao B, Yan Y. Complete genome sequence of Gordonia sp. YC-JH1, a bacterium efficiently degrading a wide range of phthalic acid esters. J Biotechnol. 2018 Aug 10;279:55-60. doi: 10.1016/j.jbiotec.2018.05.009. Epub 2018 May 12. PubMed PMID: 29763639. 9: Li X, Sun H, Yao Y, Zhao Z, Qin X, Duan Y, Wang L. Distribution of Phthalate Metabolites between Paired Maternal-Fetal Samples. Environ Sci Technol. 2018 Jun 5;52(11):6626-6635. doi: 10.1021/acs.est.8b00838. Epub 2018 May 22. PubMed PMID: 29754483. 10: Yang T, Ren L, Jia Y, Fan S, Wang J, Wang J, Nahurira R, Wang H, Yan Y. Biodegradation of Di-(2-ethylhexyl) Phthalate by Rhodococcus ruber YC-YT1 in Contaminated Water and Soil. Int J Environ Res Public Health. 2018 May 11;15(5). pii: E964. doi: 10.3390/ijerph15050964. PubMed PMID: 29751654; PubMed Central PMCID: PMC5982003. 11: Huang HB, Kuo PL, Chang JW, Jaakkola JJK, Liao KW, Huang PC. Longitudinal assessment of prenatal phthalate exposure on serum and cord thyroid hormones homeostasis during pregnancy - Tainan birth cohort study (TBCS). Sci Total Environ. 2018 Apr 1;619-620:1058-1065. doi: 10.1016/j.scitotenv.2017.11.048. Epub 2017 Nov 29. PubMed PMID: 29734584. 12: Wu W, Sheng H, Gu C, Song Y, Willbold S, Qiao Y, Liu G, Zhao W, Wang Y, Jiang X, Wang F. Extraneous dissolved organic matter enhanced adsorption of dibutyl phthalate in soils: Insights from kinetics and isotherms. Sci Total Environ. 2018 Aug 1;631-632:1495-1503. doi: 10.1016/j.scitotenv.2018.02.251. Epub 2018 Mar 28. PubMed PMID: 29727973. 13: Lee MC, Park JC, Lee JS. Effects of environmental stressors on lipid metabolism in aquatic invertebrates. Aquat Toxicol. 2018 Jul;200:83-92. doi: 10.1016/j.aquatox.2018.04.016. Epub 2018 Apr 25. PubMed PMID: 29727774. 14: Setti Ahmed K, Kharoubi O, Aoues AEK, Bouchekara M, Khaladi B, Taleb M. Effect of Gestational and Lactational Exposure to DEHP, DINP, and DEP on Intestinal Morphology, Disaccharidases, and Alkaline Phosphatase in Rats during Postnatal Development. Am J Perinatol. 2018 May 1. doi: 10.1055/s-0038-1642027. [Epub ahead of print] PubMed PMID: 29715699. 15: Miura T, Suemizu H, Goto M, Sakai N, Iwata H, Shimizu M, Yamazaki H. Human urinary concentrations of monoisononyl phthalate estimated using physiologically based pharmacokinetic modeling and experimental pharmacokinetics in humanized-liver mice orally administered with diisononyl phthalate. Xenobiotica. 2018 May 18:1-8. doi: 10.1080/00498254.2018.1471753. [Epub ahead of print] PubMed PMID: 29708805. 16: Gupta S, Gadi R. Temporal Variation of Phthalic Acid Esters (PAEs) in Ambient Atmosphere of Delhi. Bull Environ Contam Toxicol. 2018 Apr 26. doi: 10.1007/s00128-018-2337-1. [Epub ahead of print] PubMed PMID: 29700580. 17: Kang W, Zhao Y, Wang P, Li Z, Hou X, Huang Z, Yang H. Rheological behavior and mechanism of pH-responsive wormlike micelle variations induced by isomers of phthalic acid. Soft Matter. 2018 Jun 6;14(22):4445-4452. doi: 10.1039/c8sm00467f. PubMed PMID: 29693695. 18: Sawers RG. o-Phthalate derived from plastics' plasticizers and a bacterium's solution to its anaerobic degradation. Mol Microbiol. 2018 Jun;108(6):595-600. doi: 10.1111/mmi.13975. Epub 2018 May 9. PubMed PMID: 29679505. 19: Wu Y, Chen XX, Zhu TK, Li X, Chen XH, Mo CH, Li YW, Cai QY, Wong MH. Variation in accumulation, transport, and distribution of phthalic acid esters (PAEs) in soil columns grown with low- and high-PAE accumulating rice cultivars. Environ Sci Pollut Res Int. 2018 Apr 19. doi: 10.1007/s11356-018-1938-x. [Epub ahead of print] PubMed PMID: 29675815. 20: Yang J, Guo C, Liu S, Liu W, Wang H, Dang Z, Lu G. Characterization of a di-n-butyl phthalate-degrading bacterial consortium and its application in contaminated soil. Environ Sci Pollut Res Int. 2018 Apr 17. doi: 10.1007/s11356-018-1862-0. [Epub ahead of print] PubMed PMID: 29667057.