| Identification | More | [Name]
4-Hydroxyphenylacetic acid | [CAS]
156-38-7 | [Synonyms]
4-HYDROXYPHENYLACETIC ACID
AKOS 236-100
PHPA
P-HYDROPHENYLACETIC ACID
P-HYDROXYPHENYLACETIC ACID
RARECHEM AL BO 0188
(p-hydroxyphenyl)-aceticaci
4-carboxymethylphenol
4-Hydroxybenzeneacetic acid
4-hydroxy-benzeneaceticaci
4-hydroxybenzeneaceticacid
4-hydroxyphenylethanoicacid
Acetic acid, (p-hydroxyphenyl)-
ethanoicacid,4-hydroxyphenyl-
Parahydroxy phenylacetic acid
4-HYDROXYPHENYLACETIC ACID, FOR FLUORESC ENCE
4-HydroxyphenylacetidAcid
Benzeneacetic acid, 4-hydroxy-
2-(4-hydroxyphenyl)acetic acid
4-Hydroxyphenylacetic acid 98% | [EINECS(EC#)]
205-851-3 | [Molecular Formula]
C8H8O3 | [MDL Number]
MFCD00004347 | [Molecular Weight]
152.15 | [MOL File]
156-38-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white to cream or light tan crystalline powder | [Melting point ]
148-151 °C(lit.)
| [Boiling point ]
234.6°C (rough estimate) | [density ]
1.2143 (rough estimate) | [vapor pressure ]
0.007Pa at 25℃ | [refractive index ]
1.4945 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
50g/l | [form ]
Crystalline Powder | [pka]
4.50±0.10(Predicted) | [color ]
White to cream or light tan | [PH]
2.0-2.4 (30g/l, H2O, 20℃) | [Water Solubility ]
Soluble in dimethyl sulfoxide and methanol. Slightly soluble in water. | [BRN ]
1448766 | [InChI]
1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) | [InChIKey]
XQXPVVBIMDBYFF-UHFFFAOYSA-N | [SMILES]
OC(=O)Cc1ccc(O)cc1 | [LogP]
0.75 at 25℃ | [CAS DataBase Reference]
156-38-7(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzeneacetic acid, 4-hydroxy-(156-38-7) | [EPA Substance Registry System]
156-38-7(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
AI2680000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29182990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Questions And Answer | Back Directory | [Description]
4-Hydroxyphenylacetic acid is an acetate derivative used in the acylation of phenols and amines1. It is an active component of Chinese herb Aster tataricus which had been widely used in China for the treatment of pulmonary diseases, HBV, and carcinoma. It is an active metabolite of amino acid metabolism. Study has also shown that it can attenuate inflammation and edema through suppressing hypertonic and hypoxic induction of HIF-1α in seawater aspiration-induced lung injury in rats. In chemical industry, it is an intermediate used to synthesize atenolol and 3, 4-dihydroxyphenylacetic acid.
| [Referrence]
[1] Liu, Zhongyang, et al. "4-Hydroxyphenylacetic Acid Attenuated Inflammation and Edema via Suppressing HIF-1α in Seawater Aspiration-Induced Lung Injury in Rats." International Journal of Molecular Sciences 15.7(2014):12861-84.
[2] Ng, T.B.; Liu, F.; Lu, Y.; Cheng, C.H.; Wang, Z. Antioxidant activity of compounds from the medicinal herb Aster tataricus. Comp. Biochem. Physiol. 2003, 136, 109–115.
[3] Du, L.; Mei, H.F.; Yin, X.; Xing, Y.Q. Delayed growth of glioma by a polysaccharide from Aster tataricus involve upregulation of Bax/Bcl-2 ratio, activation of caspase-3/8/9, and downregulation of the Akt. Tumour Biol. 2014, 35, 1819–1825.
[4] Zhang, Z., Liu, J., Li, Y., Wang, Y., Zheng, X., Wang, F., Tong, T., Miao, D., Li, W., Chen, L., & Wang, L. (2024). 4-Hydroxyphenylacetic Acid, a microbial-derived metabolite of Polyphenols, inhibits osteoclastogenesis by inhibiting ROS production. International Immunopharmacology, 143, Article 113571. https://doi.org/10.1016/j.intimp.2024.113571
|
| Hazard Information | Back Directory | [Chemical Properties]
white to cream or light tan crystalline powder | [Uses]
A compound present in olive oil. An important fine chemical intermediate with broad prospects for application development. | [Definition]
ChEBI: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. | [Preparation]
4-Hydroxyphenylacetic acid is synthesized by diazotization and hydrolysis of 4-aminophenylacetic acid.
4-aminophenylacetic acid and alkali solution are prepared into sodium salt, and then sulfuric acid is added. Cool to 0°C, control the temperature at 0-5°C, and add sodium nitrate solution dropwise, and the reaction is completed for 0.5h. The obtained diazonium was added dropwise to dilute sulfuric acid at 90-95°C for about 1 hour, and the reaction was continued for 1 hour. The reaction solution was decolorized and filtered, cooled and extracted with ethyl acetate, and the extract was recovered with ethyl acetate to obtain 4-Hydroxyphenylacetic acid. The yield is about 85%. | [Flammability and Explosibility]
Notclassified | [Biological Activity]
4-Hydroxyphenylacetic acid (4-HPA) is an important microbial-derived metabolite of polyphenols in the intestinal tract[4]. | [Purification Methods]
Crystallise the acid from water or Et2O/pet ether. The p-bromophenacyl ester has m 117o (from EtOH). [Beilstein 10 II 112, 10 III 430, 10 IV 543.] |
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| Company Name: |
J & K SCIENTIFIC LTD.
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| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
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| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
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| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Jia Xing Isenchem Co.,Ltd
|
| Telephone: |
0573-85285100 18627885956 |
| Website: |
https://www.chemicalbook.com/ShowSupplierProductsList14265/0_EN.htm |
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