4-Hydroxyisophthalic acidCAS# 636-46-4 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 636-46-4 | SDF | Download SDF |
PubChem ID | 12490 | Appearance | White powder |
Formula | C8H6O5 | M.Wt | 182.1 |
Type of Compound | Phenols | Storage | Desiccate at -20°C |
Synonyms | 4-Hydroxy 1,3-benzenedicarboxylic acid | ||
Solubility | Soluble in diethyl ether, DMSO and methanol; slightly soluble in water | ||
Chemical Name | 4-hydroxybenzene-1,3-dicarboxylic acid | ||
SMILES | C1=CC(=C(C=C1C(=O)O)C(=O)O)O | ||
Standard InChIKey | BCEQKAQCUWUNML-UHFFFAOYSA-N | ||
Standard InChI | InChI=1S/C8H6O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H,(H,10,11)(H,12,13) | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | 4-Hydroxyisophthalic acid has analgesic and antipyretic activities.It could be a promising natural antioxidant and a neuroprotective molecule targeting oxidative stress-mediated mitochondrial dysfunction with therapeutic potential for neurodegenerative disorders. |
4-Hydroxyisophthalic acid Dilution Calculator
4-Hydroxyisophthalic acid Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 5.4915 mL | 27.4574 mL | 54.9149 mL | 109.8298 mL | 137.2872 mL |
5 mM | 1.0983 mL | 5.4915 mL | 10.983 mL | 21.966 mL | 27.4574 mL |
10 mM | 0.5491 mL | 2.7457 mL | 5.4915 mL | 10.983 mL | 13.7287 mL |
50 mM | 0.1098 mL | 0.5491 mL | 1.0983 mL | 2.1966 mL | 2.7457 mL |
100 mM | 0.0549 mL | 0.2746 mL | 0.5491 mL | 1.0983 mL | 1.3729 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- Syringetin
Catalog No.:BCN9875
CAS No.:4423-37-4
- Norharman
Catalog No.:BCN9874
CAS No.:244-63-3
- 2-(4-Hydroxybenzal)acetophenone
Catalog No.:BCN9873
CAS No.:20426-12-4
- Condurango glycoside A
Catalog No.:BCN9872
CAS No.:11051-90-4
- Lappaconine
Catalog No.:BCN9871
CAS No.:23943-93-3
- Cannabiscitrin
Catalog No.:BCN9870
CAS No.:520-14-9
- Datiscin
Catalog No.:BCN9869
CAS No.:16310-92-2
- 15-Methoxy-16-oxo-15,16H-strictic acid
Catalog No.:BCN9868
CAS No.:1356388-38-9
- 1,2-Dimethoxybenzene
Catalog No.:BCN9867
CAS No.:91-16-7
- Tropic acid
Catalog No.:BCN9866
CAS No.:529-64-6
- 4-(4-Methoxyphenyl)-2-butanone
Catalog No.:BCN9865
CAS No.:104-20-1
- ICG-001
Catalog No.:BCN9864
CAS No.:780757-88-2
- Lyciumamide B
Catalog No.:BCN9877
CAS No.:1647111-41-8
- Tricaprin
Catalog No.:BCN9878
CAS No.:621-71-6
- Dihydroquinine
Catalog No.:BCN9879
CAS No.:522-66-7
- Cymarin
Catalog No.:BCN9880
CAS No.:508-77-0
- 5,7-Dihydroxy 3,3',4',5',6,8-hexamethoxyflavone
Catalog No.:BCN9881
CAS No.:96887-18-2
- gamma-Decalactone
Catalog No.:BCN9882
CAS No.:706-14-9
- 2-(2-Hydroxybenzal)acetophenone
Catalog No.:BCN9883
CAS No.:644-78-0
- (1S,2S,5S)-(-)-Myrtanol
Catalog No.:BCN9884
CAS No.:53369-17-8
- 6-Methoxyflavanone
Catalog No.:BCN9885
CAS No.:3034-04-6
- 15-Deoxypulic acid
Catalog No.:BCN9886
CAS No.:95523-05-0
- 4-Oxadocosane-1,2-diol
Catalog No.:BCN9887
CAS No.:544-62-7
- Tribulosin
Catalog No.:BCN9888
CAS No.:79974-46-2
Natural bioactive 4-Hydroxyisophthalic acid (4-HIPA) exhibited antiproliferative potential by upregulating apoptotic markers in in vitro and in vivo cancer models.[Pubmed:32607952]
Mol Biol Rep. 2020 Jul;47(7):5343-5353.
There is tremendous scope for identifying novel anti-cancer molecules from the unexplored reserves of plant kingdom. The application of dietary supplementation or medicine derived from such sources is a promising approach towards treatment of cancer. In the present study we have evaluated the antiproliferative potential of 4-Hydroxyisophthalic acid (4-HIPA), which is a novel antioxidant compound isolated from the roots of the aqueous extract of Decalepis hamiltonii. 4-HIPA was screened in vitro against human breast cancer cell lines MCF-7, MDA-MB-468 and normal human breast epithelial cell MCF-10, and demonstrated that human breast cancer cell lines, in contrast to MCF-10, are sensitive to 4-HIPA .4-HIPA showed marked reduction in cell viability and short-term proliferation assays in these cells. Results of the long-term colony formation and scratch assay further reaffirmed that 4-HIPA inhibited the growth and proliferation in breast cancer cells. We further conducted in vivo studies using murine Ehrlich Ascites Tumor (EAT) cell model. Our in vivo results established that treatment with 4-HIPA reduced the tumorigenesis by promoting apoptosis in EAT-bearing mice. The results of our molecular docking predictions further warranted our claim. This study is valuable as 4-HIPA exhibits antiproliferative potential that can be exploited in the development of anticancer drugs.
Neuroprotective action of 4-Hydroxyisophthalic acid against paraquat-induced motor impairment involves amelioration of mitochondrial damage and neurodegeneration in Drosophila.[Pubmed:29653138]
Neurotoxicology. 2018 May;66:160-169.
Neurodegenerative disorders including Parkinson's disease (PD) are believed to be caused by oxidative stress and mitochondrial dysfunction. Exposure to environmental agents such as pesticides has been implicated in the etiology of sporadic PD. Paraquat (PQ), a widely used herbicide, induces PD symptoms in laboratory animals including Drosophila. PQ acts as a free radical generator and induces oxidative damage, which is implicated in neuronal cell death. Drosophila model of PQ-induced PD offers a convenient tool for mechanistic studies and, to assess the neuroprotective potential of natural antioxidants. We have investigated the neuroprotective potential of 4-Hydroxyisophthalic acid (DHA-I), a novel bioactive molecule from the roots of Decalepis hamiltonii, against PQ-induced locomotor impairment and neurodegeneration in Drosophila melanogaster. Our study shows that PQ treatment results in movement disorder associated with oxidative stress-mediated mitochondrial damage and neurodegeneration in the brain as evident by ultrastructural observations. Treatment with DHA-I markedly attenuated locomotor deficits, oxidative stress, mitochondrial damage, and neurodegenerative changes induced by PQ in Drosophila. Our results show that DHA-I could be a promising natural antioxidant and a neuroprotective molecule targeting oxidative stress-mediated mitochondrial dysfunction with therapeutic potential for neurodegenerative disorders.
Modulatory Effects of Decalepis hamiltonii Extract and Its Compounds on the Antioxidant Status of the Aging Rat Brain.[Pubmed:28584487]
J Pharm Bioallied Sci. 2017 Jan-Mar;9(1):8-15.
OBJECTIVE: The present study was aimed to investigate the neuroprotective effects of Decalepis hamiltonii (Dh) aqueous root extract and its compounds against age-related oxidative stress (OS) in the discrete regions of the rat brain. MATERIALS AND METHODS: Male Wistar albino rats of 4- and 22-month-old were divided into control and six supplemented groups. The supplemented groups were orally administered with ellagic acid (EA), 4-Hydroxyisophthalic acid (4-HIA), and Dh extract for 30 days. RESULTS: Age-related decrease in antioxidant enzyme activities was noticed. The hippocampus was found to be more vulnerable to OS as seen by the elevation in the OS markers. Supplementation of the Dh extract, EA, and 4-HIA was found to be effective in up-regulating the antioxidant status. However, the extent of up-regulation was more evident in Dh supplemented animals. CONCLUSION: Our results suggest that Dh extract and its compounds exhibit neuroprotective effects against age-related OS and can be used as a dietary therapeutic intervention for the treatment of neurological disorders.
4-Hydroxyisophthalic acid from Decalepis hamiltonii rescues the neurobehavioral deficit in transgenic Drosophila model of taupathies.[Pubmed:27615061]
Neurochem Int. 2016 Nov;100:78-90.
Oxidative stress is one of the major etiological factors implicated in pathogenesis of neurodegenerative diseases. Since neurons are more sensitive to oxidative damage there is an increasing interest in developing novel antioxidant therapies, especially herbal preparations due to their safety profile and high efficiency. In this regard, the neuroprotective potential of a novel antioxidant compound, 4-Hydroxyisophthalic acid (4-HIPA) isolated from aqueous extract of Decalepis hamiltonii roots was examined using transgenic Drosophila model of taupathy expressing wild-type and mutant forms of 2N4R isoform of human microtubule associated protein tau (MAPT). Taupathy model flies showed cognitive deficits in olfactory memory and deteriorated circadian rhythm of locomotory activities. Administration of 0.1 mg/ml 4-HIPA, markedly enhanced their olfactory memory performance and restored circadian rhythmicity of the transgenic flies locomotory behavior to the normal range. The mechanism of action that underlies 4-HIPA neuroprotection involves enhancement in efficiency of cellular antioxidant defense system by means of elevation in antioxidant enzyme activities and attenuation of oxidative stress. The molecule could positively affect the activity of neurotransmitter enzymes, which in turn enhances neuronal function and ameliorates the Tau-induced neurobehavioral deficits. Our findings showed that 4-HIPA can be considered as a suitable therapeutic candidate for drug development towards treatment of neurodegenerative disorders.
[Constituents of Gymnadenia conopsea].[Pubmed:21322946]
Zhongguo Zhong Yao Za Zhi. 2010 Nov;35(21):2852-61.
OBJECTIVE: To investigate the chemical constituents of tuber of Gymnadenia conopsea. METHOD: The constituents were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and C-18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic data analysis. RESULT: Thirty-four compounds were isolated. Their structures were identified as six 2-isobutyltartrate benzyl ester glucosides: coelovirin A (1), coelovirin B (2), coelovirin E (3), coelovirin D (4), dactylorhin B (5) and loroglossin (6). Three 2-isobutylmalate benzyl ester glucosides: dactylorhin A (7), dactylorhin E (8) and militarine (9). Three lignans: arctigenin (10), lappaol A (11) and lappaol F (12). Six aromatic acid (alhyde or alcohol) derivatives: 4-beta-D-glucopyranosyloxyl-trans-phenylpropenoic acid (13), 4-beta-D-glucopyranosyloxyl-cis-phenylpropenoic acid (14), gastrodin (15), 4-beta-D-glucopyranosyloxylphenylaldehyde (16), 4-beta-D-glucopyranosyloxylbenzyl methyl ether (17), 4-beta-D-glucopyranosyloxyloxylbenzyl ethyl ether (18), and bis(4-hydroxybenzyl) ether mono 4-O-beta-D-glucopyranoside (19). Four cyclodipeptides: cyclo(L-Leu-L-Tyr) (20), cyclo(L-Leu-L-Pro) (21), cyclo(L-Val-L-Tyr) (22), and cyclo(L-Ala-D-Phe) (23). One N6-substituted andenosine: N6-(4-hydroxybenzyl)-adenine riboside (24). An aromatic amide: N-trans-feruloyltyramine (25). Nine aromatic acids (or aldehyde or alcohol): 3-hydroxybenzoic acid (26), 4-Hydroxyisophthalic acid (27), 4-hydroxybenzyl alcohol (28), 4-hydroxybenzyl methyl ether (29), 4-hydroxybenzylaldehyde (30), 4-hydroxybenzoic acic (31), 4-hydroxy-3-methoxybenzoic acid (32), trans-p-hydroxyphenylpropenoic acid (33), and cis-p-hydroxyphenylpropenoic acid (34). At a concentration of 1.0 x 10(-6) mol x L(-1), compounds 10-12 showed antioxidative activity inhibiting Fe(+2) -cystine induced rat liver microsomal lipid peroxidation with inhibitory rates of 53%, 59%, and 52%, respectively(positive control VE with 35% inhibition). CONCLUSION: These compounds were obtained from the genus Gymnadenia for the first time except for 5-7, 9, 15, 28-34. Compounds 10-12 possess antioxidant activity.
Biological activity of 4-hydroxyisophthalic acid derivatives. III. Variously substituted anilides with antimicrobial activity.[Pubmed:3994839]
Boll Soc Ital Biol Sper. 1985 Feb 28;61(2):199-204.
A series of 1,3-bis-anilides of 4-Hydroxyisophthalic acid was prepared and investigated for antibacterial and antifungal activities. The prepared compounds (I-XIV), of the general formula (A), where Xn = 2-NO2 (I); 2,4-(NO2)2 (II); 2,4-NO2, Cl (III); 2,4-NO2,CF3 (IV); 3,4-NO2,Cl (V); 2,4-Cl,NO2 (VI); 2,5-Cl,NO2 (VII); 2,4,6-Cl,NO2,Cl (VIII); 2,4-Br, NO2 (IX); 2-CF3 (X); 3-CF3 (XI); 2,5-Cl,CF3 (XII); 2,5-CH3,Cl (XIII); 3,4-Cl,CH3 (XIV), were obtained in satisfactory yield by reacting 4-Hydroxyisophthalic acid with the appropriate substituted aniline. (Formula: see text). The prepared compounds were tested for antimicrobial activity by a disk-diffusion assay (Kirby-Bauer modified). The organisms used were the following: S. aureus, B. subtilis, B. anthracis, M. paratuberculosis 607, E. coli Bb, S. typhi, S. typhimurium, S. paratyphi B, Pr. vulgaris, K1. pneumoniae, Ps. aeruginosa, C. albicans, and A. niger. The results of the antimicrobial screening showed that a number of substituted anilides exhibited varying degrees of activity against Gram-positive and Gram-negative bacteria, and fungi, nitro-halogen-derivatives being the most interesting members of the series.
Biological activity of 4-hydroxyisophthalic acid derivatives. II. Anilides with antimicrobial activity.[Pubmed:6543319]
Boll Soc Ital Biol Sper. 1984 Dec 30;60(12):2273-9.
A series of 1,3 -bis-anilides of 4-Hydroxyisophthalic acid was prepared and tested for antibacterial and antifungal activity. The prepared compounds (I-XVIII), of general structure (A), (Formula: see text) where Xn = H (I); 2-F (II); 3-F (III); 4-F (IV); 2-Cl (V); 3-Cl (VI); 4-Cl (VII); 2-Br (VIII); 3-Br (IX); 4-Br (X); 2-J (XI); 3-J (XII); 4-J (XIII); 2,5-Cl2 (XIV); 2,4-Br2 (XV); 2,3,4-Cl3 (XVI), 2,4,5-Cl3 (XVII); 2,4,6-Cl3 (XVIII), were investigated for the purpose of determining the effect of halogen-substitution on the aniline rings of (A). All of these compounds were prepared in satisfactory hield by reaction of 4-Hydroxyisophthalic acid with the appropriate aromatic amine at 175 degrees for 3 hours. The 1,3-bis-anilides prepared in this investigation were screened for antimicrobial activity by a disk-diffusion assay (Kirby-Bauer modified). The organisms used were laboratory cultures of S. aureus, B. subtilis, B. anthracis, M. paratuberculosis 607, E. coli Bb, S. typhi, S. typhimurium, S. paratyphi B, Pr. vulgaris, Kl. pneumoniae, Ps. aeruginosa, C. albicans, and A. niger. The results of this investigation indicated that most of the 1,3-bis-(halogen-anilides) of 4-Hydroxyisophthalic acid had little or no antifungal activity "in vitro", while showed significant activity against Gram+ and Gram- bacteria. Some fluoro-derivatives showed inhibitory activity especially toward S. aureus and M. paratuberculosis. Iodo-derivatives showed broad-spectrum "in vitro" antimicrobial activity, and had some antifungal activity.
Biological activity of 4-hydroxyisophthalic acid derivatives. Hydrazones with antimicrobial activity.[Pubmed:6477732]
Boll Soc Ital Biol Sper. 1984 Jun 30;60(6):1169-75.
The following hydrazono derivatives (I-XIX) of type (A) (sequence in text) where Rn = (sequence in text ) (I-XVII); (sequence in text) (XVIII); -CCl3 (XIX); and Xn = H (I); 2-Cl (II); 3-Cl (III); 4-Cl (IV); 2-NO2 (V); 3-NO2 (VI); 4-NO2 (VII); 2-OH (VIII); 3-OH (IX); 4-OH (X); 4-F (XI); 3,4-OCH3,OH (XII); 3,4,5-OCH3,OH,J (XIII); 3,4-OCH3,OCH3 (XIV); 2,4-Cl2 (XV); 3,4-Cl2 (XVI); 2,6-Cl2 (XVII); were prepared and characterized in an attempt to make available for testing a representative selection of hitherto unreported 4-Hydroxyisophthalic acid derivatives. The new compounds in question were obtained in satisfactory yield by condensation of 4-Hydroxyisophthalic acid hydrazide with the appropriate aldehydes. The prepared compounds were tested for their possible activity against Gram-positive (S. epidermidis, B. subtilis, B. anthracis) and Gram-negative bacteria (P. aeruginosa, B. melitensis, S. typhi O, S. typhi H, S. infantis, S. paratyphi B, E. coli Bb, E. coli 7075), and fungi (C. albicans, A. niger, S. cerevisiae). The "in vitro" antimicrobial assays were carried out using the paper disk technique (Kirby-Bauer modified). The influence of certain structural modifications on the antimicrobial activity was evaluated.