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| Other Sizes |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Probably excreted as phthalic acid. /From table/ Metabolism / Metabolites Yields 4,5-dihydroxyphthalic acid in Pseudomonas. /FROM TABLE/ Dose effects of di(2-ethylhexyl)phthalate distribution, excretion, and binding to macromolecules were studied in rodents. The urinary di(2-ethylhexyl)phthalate metabolite profile was similar for all doses, except that free phthalic acid was 6 times greater on days 3 and 10 at the highest compared to the lowest dose. The metabolism of di-(5-hexenyl)phthalate and di-(9-decenyl)phthalate was investigated in rats. Male CD rats received two oral doses of 3 to 12 uM/kg radiolabeled or unlabeled di-(5-hexenyl)phthalate and di-(decenyl)phthalate in cottonseed oil 24 hr apart. One third of the radioactivity was found in the urine. The metabolites were identified as mono-5-hexenyl-phthalate. Mono-5-hexenyl-phthalate comprised 21% of the total urinary phthalates while 5-hexenyl-phthalate glucuronide amounted to 13.2% and free 5-hexenyl-phthalate to 7.8%. In contrast no metabolites of di-(9-decenyl)phthalate were excreted as glucuronide conjugates and only a trace of free phthalic acid was detected although 40 to 50% of the compound was recovered in the urine. The distribution of the metabolic phthalates indicated a different metabolic pathway for di-(9-decenyl)phthalate and di-(5-hexenyl)phthalate. /It was/ concluded that the chemically reactive epoxide metabolite of phthalate with unsaturated side chains may play a role in the acute toxicity of di-(5-hexenyl)phthalate and di-(9-decenyl)phthalate. Phthalate grown cells readily oxidized dibutylphthalate, phthalate, 3,4-dihydroxyphthalate and protocatechuate. Phthalate-3,4-dioxygenase (and possibly the dihydrodiol dehydrogenase) was induced by phthalate or a metabolite and subsequent enzymes were inducible by protocatechuate or a subsequent metabolic product. During growth at 37 °C, strain 12B gave clones at high frequency that had lost the ability to grow with phthalate esters. For more Metabolism/Metabolites (Complete) data for PHTHALIC ACID (6 total), please visit the HSDB record page. |
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| Toxicity/Toxicokinetics |
Non-Human Toxicity Values
LD50 Mouse ip 550 mg/kg LD50 Mouse oral 2,530 mg/kg LD50 Rat oral 7.9 g/kg |
| References | |
| Additional Infomation |
Phthalic acid appears as white crystals or fine white powder. (NTP, 1992)
Phthalic acid is a benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions. It has a role as a human xenobiotic metabolite. It is a conjugate acid of a phthalate(1-). Phthalic acid has been reported in Papaver somniferum, Cocos nucifera, and other organisms with data available. Mechanism of Action Although it is well established that high dose administration of di(2-ethylhexyl)phthalate and its monoester metabolite induces severe testicular atrophy in rats the mechanisms of this testicular injury Is not clear. The present experiment was undertaken to examine the effects of di(2-ethylhexyl) phthalate and mono(2-ethylhexyl)phthalate on mitochondrial functions of rat testis. Di(2-ethylhexyl)phthalate and di-n-octyl phthalate, a di(2-ethylhexyl) phthalate isomer which causes less severe testicular injury did not inhibit the state 3 oxygen consumption up to 0.65 umol/mL in vitro. On the other hand, mono(2-ethylhexyl)phthalate and mono-n-octyl phthalate a metabolite of di-n-octyl phthalate inhibited the state 3 oxygen-consumption down to a concentration of 0.065 amble/mL. Testicular mitochondrial respiratory functions of rats administered 2 g/kg di(2-ethylhexyl) phthalate were lower than those of control or di-n-octyl phthalate treated rats. These differences were verified by characteristics of pharmacokinetic parameters and testicular concentrations of mono(2-ethylhexyl)phthalate and mono-n-octyl phthalate. It nay be suggested that a possible mechanism of testicular atrophy induced by di(2-ethylhexyl) phthalate may be due to direct inhibition by mono(2-ethylhexyl)phthalate (and partially di(2-ethylhexyl)phthalate) of the respiratory functions of Sertoli cell mitochondria in rat testis. ... phthalic acid and nonylphenol stimulated PXR-mediated transcription at concentrations comparable to those at which they activate estrogen receptor-mediated transcription using a transient reporter gene expression assay in COS-7 cells. |
| Molecular Formula |
C8H6O4
|
|---|---|
| Molecular Weight |
166.13
|
| Exact Mass |
166.026
|
| CAS # |
88-99-3
|
| Related CAS # |
Phthalic acid-d4;87976-26-9
|
| PubChem CID |
1017
|
| Appearance |
White to off-white solid powder
|
| Density |
1.5±0.1 g/cm3
|
| Boiling Point |
378.3±25.0 °C at 760 mmHg
|
| Melting Point |
210-211 °C (dec.)(lit.)
|
| Flash Point |
196.7±19.7 °C
|
| Vapour Pressure |
0.0±0.9 mmHg at 25°C
|
| Index of Refraction |
1.618
|
| LogP |
0.81
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
12
|
| Complexity |
177
|
| Defined Atom Stereocenter Count |
0
|
| 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)
|
| Chemical Name |
phthalic acid
|
| Synonyms |
NSC-5348; NSC 5348; Phthalic acid
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~601.94 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.05 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (15.05 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (15.05 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.0194 mL | 30.0969 mL | 60.1938 mL | |
| 5 mM | 1.2039 mL | 6.0194 mL | 12.0388 mL | |
| 10 mM | 0.6019 mL | 3.0097 mL | 6.0194 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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