p-Hydroxyphenylacetic acid
4-Hydroxyphenylacetic acid
CAS: 156-38-7
Molecular Formula: C8H8O3
p-Hydroxyphenylacetic acid - Names and Identifiers
| Name | 4-Hydroxyphenylacetic acid |
| Synonyms | NSC 27460 4-carboxymethylphenol Arbidol Impurity F HCl (4-hydroxyphenyl)acetate p-Hydroxyphenylacetic acid 4-Hydroxyphenylacetic acid (p-hydroxyphenyl)-aceticaci 4-Hydroxybenzeneacetic acid p-Hydroxy Phenyl Acetic Acid Levothyroxine Sodium Impurity d Acetic acid, (p-hydroxyphenyl)- |
| CAS | 156-38-7 |
| EINECS | 205-851-3 |
| InChI | InChI=1/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)/p-1 |
| InChIKey | XQXPVVBIMDBYFF-UHFFFAOYSA-N |
p-Hydroxyphenylacetic acid - Physico-chemical Properties
| Molecular Formula | C8H8O3 |
| Molar Mass | 152.15 |
| Density | 1.2143 (rough estimate) |
| Melting Point | 148-151°C(lit.) |
| Boling Point | 234.6°C (rough estimate) |
| Flash Point | 177.6°C |
| Water Solubility | Soluble in dimethyl sulfoxide and methanol. Slightly soluble in water. |
| Solubility | Soluble in ethanol, ether and hot water |
| Vapor Presure | 0.007Pa at 25℃ |
| Appearance | White Crystals |
| Color | White to cream or light tan |
| BRN | 1448766 |
| pKa | 4.50±0.10(Predicted) |
| PH | 2.0-2.4 (30g/l, H2O, 20℃) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Sensitive | Sensitive to light and air |
| Refractive Index | 1.4945 (estimate) |
| MDL | MFCD00004347 |
| Physical and Chemical Properties | Melting point 147-152°C |
| Use | Is the synthesis of new drugs 4, 7-dihydroxyisoflavone intermediates, can also be used as pesticide intermediates |
p-Hydroxyphenylacetic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 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 |
| TSCA | Yes |
| HS Code | 29182990 |
| Hazard Note | Irritant |
p-Hydroxyphenylacetic acid - Upstream Downstream Industry
| Raw Materials | Phenol Glyoxal Glyoxylic acid |
| Downstream Products | 4-Hydroxybenzeneacetamide Methyl 4-hydroxyphenylacetate Ethyl 4-hydroxyphenylacetate bufexamac |
p-Hydroxyphenylacetic acid - Reference
| Reference Show more | 1. Kang Chao, Hao Du, Jian Sijie, Rong Na, Liu Xiang, Ding Rui. Evaluation of the metabolic effects of phenylacetic acid at different hydroxyl sites on four liver microsomal enzymes by probe drug method [J]. Journal of Shaanxi University of Technology (Natural Science Edition),2021,37(01):50-56 78. 2. Ge, Zhen-zhen, et al. "Metabolites and changes in antioxidant activity of A- type and B- type proanthocyanidin dimers after incubation with rat intestinal microbiota." Journal of agricultural and food chemistry 63.41 (2015): 8991-8998.https:// doi.org/10.1021 3. [IF = 5.279] Zhen-zhen Ge et al. "Metabolites and Changes in Antioxidant Activity of A- Type and B- Type Proanthocyanidin Dimers after Incubation with Rat Intestinal Microbiota." J Agr Food Chem. 2015;63(41): 8991-8998 4. [IF = 4.952] Yuxin Hao et al. "Stability and mechanism of phenolic compounds from raspberry extract under in vitro gastrointestinal digestion." Lwt Food Sci Technol. 2021 Mar;139:110552 5. [IF = 4.24] Nana Li et al. "Characterization of phenolic compounds and anti-acetylcholinase activity of coconut shells." Food Biosci. 2021 Aug;42:101204 6. [IF = 4.952] Yulong Wei et al. "Characterization of blueberry (Vaccinium corymbosum L.) catechol oxidases III binding mechanism in response to selected substrates and inhibitors." Lwt Food Sci Technol. 2022 Mar;158:113142 |
p-Hydroxyphenylacetic acid - Nature
Open Data Verified Data
white or yellowish crystalline powder. The melting point was 149-151 °c.
Last Update：2024-01-02 23:10:35
p-Hydroxyphenylacetic acid - Preparation Method
Open Data Verified Data
- the total yield of p-aminophenylacetic acid method is about 85%.
- 3 fluoro-p-hydroxyphenylacetic acid.
Last Update：2022-01-01 10:43:32
p-Hydroxyphenylacetic acid - Use
Open Data Verified Data
This product is used for the synthesis of beta receptor blocking drug atenolol and Pueraria daidzein active ingredient -4,7-hydroxyisoflavone; Also can be used as pesticide intermediates.
Last Update：2022-01-01 10:43:32
p-Hydroxyphenylacetic acid - Safety
Open Data Verified Data
packaged in 25kg carton.
Last Update：2022-01-01 10:43:33
p-Hydroxyphenylacetic acid - Reference Information
| LogP | 0.75 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Biological activity | 4-Hydroxyphthalic acid (p-Hydroxyphenylacetic acid, parahydroxy phenylacetate) is a compound found in olive oil and beer, as a chemical The intermediate is used to synthesize atenolol (atenolol) and 3, 4-dihydroxyphthalic acid. |
| Use | Biochemical research Organic synthesis. Organic synthesis intermediates for the production of β-receptor blockers Atenolol and Pueraria daidzein active ingredient -4, 7-dihydroxyisoflavones; also used as pesticide intermediates. Acylation reagents for phenolic compounds and amine compounds. It is an intermediate for the synthesis of a new drug 4, 7-dihydroxyisoflavone, and can also be used as a pesticide intermediate |
| Production method | 1. It is obtained by diazotization and hydrolysis of p-aminophenylacetic acid. Prepare p-aminophenylacetic acid and alkali solution into sodium salt, and then add sulfuric acid. Cold to 0 ℃, control the temperature to add sodium nitrate solution dropwise at 0-5 ℃, and finish the reaction for 0.5h.. The obtained diazo droplets were added to dilute sulfuric acid at 90-95°C, and the dripping was completed for about 1h, and the reaction was continued for 1h. The reaction solution is decolorized and filtered, cooled and extracted with ethyl acetate, and the extract recovers ethyl acetate to obtain the finished product. The yield is about 85%. 2.3-fluoro p-hydroxyphenylacetic acid. |
Last Update：2024-04-09 20:49:11
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Raw Materials for p-Hydroxyphenylacetic acid
Downstream Products for p-Hydroxyphenylacetic acid