3-(4-hydroxyphenyl)propanoic acid
P-Hydroxybenzene propanoic acid
CAS: 501-97-3
Molecular Formula: C9H10O3
3-(4-hydroxyphenyl)propanoic acid - Names and Identifiers
| Name | P-Hydroxybenzene propanoic acid |
| Synonyms | Phloretate Phloretic acid PHLORETIC ACID DESAMINOTYROSINE PHLORETINIC ACID 4-hydroxybenzenepropanoic 4-Hydroxyhydrocinnamic acid 4-hydroxyphenylpropionicacid 4-hydroxybenzenepropanoicacid 4-Hydroxyphenylpropionic acid 3-(4-hydroxyphenyl)propanoate 4-hydroxy-benzenepropanoicaci 4-Hydroxybenzenepropanoic acid p-Hydroxyphenylpropionic acid p-Hydroxyphenyl-propionic acid P-Hydroxybenzene propanoic acid 2-(4-hydroxyphenyl)propanoic acid 3-(4-Hydroxyphenyl)propionic acid Benzenepropanoic acid, 4-hydroxy- 3-(4-hydroxyphenyl)propanoic acid 3-(para-Hydroxyphenyl)-propionic acid |
| CAS | 501-97-3 |
| EINECS | 207-931-3 |
| InChI | InChI=1/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)/p-1 |
| InChIKey | NMHMNPHRMNGLLB-UHFFFAOYSA-N |
3-(4-hydroxyphenyl)propanoic acid - Physico-chemical Properties
| Molecular Formula | C9H10O3 |
| Molar Mass | 166.17 |
| Density | 1.1708 (rough estimate) |
| Melting Point | 129-131°C(lit.) |
| Boling Point | 254.38°C (rough estimate) |
| Flash Point | 181.1°C |
| Water Solubility | slightly soluble |
| Solubility | Slightly soluble |
| Vapor Presure | 1.43E-05mmHg at 25°C |
| Appearance | Light-yellow crystal |
| Color | Off-white to beige |
| BRN | 2209841 |
| pKa | 4.74±0.10(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Refractive Index | 1.5286 (estimate) |
| MDL | MFCD00002778 |
| Physical and Chemical Properties | Melting point 126-130°C water-soluble snyly soluble |
| Use | Used as a pharmaceutical Intermediate |
| In vivo study | Wild-type mice produce nanomoles of Desaminotyrosine per gram of feces and have picomolar quantities of Desaminotyrosine in the serum. Desaminotyrosine (200 mM) treatment before influenza infection, protects from influenza by type I interferon (IFN) signaling, with no effect on weight loss or survival in mice with or without vancomycin, neomycin, ampicillin, and metronidazole (VNAM). Desaminotyrosine enhances type I IFN in macrophages via type I IFN amplification in mice. |
3-(4-hydroxyphenyl)propanoic 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. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | MW5342000 |
| HS Code | 29182990 |
| Hazard Note | Irritant |
| Toxicity | LD50 intravenous in mouse: 1809mg/kg |
3-(4-hydroxyphenyl)propanoic acid - Reference
| Reference Show more | 1. Guo, Xiao, et al. "Intestinal absorption and distribution of naringin, hesperidin, and their metabolites in mice." Journal of Functional Foods 74 (2020): 104158.https://doi.org/10.1016/j.jff.2020.104158 2. [IF=3.757] Yuchen Wang et al."Metabolic profile of ginkgo kernel juice fermented with lactic aicd bacteria: A potential way to degrade ginkgolic acids and enrich terpene lactones and phenolics."Process Biochem. 2019 Jan;76:25 3. [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 4. [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 5. [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 |
3-(4-hydroxyphenyl)propanoic acid - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Introduction | p-hydroxyphenylpropionic acid is also called phloretin acid. White to light yellow crystals. Insoluble in benzene and chloroform, soluble in ethanol, ether, ethyl acetate and hot water. The adjacent position will show color when it meets ferric chloride, but the opposite position will not show color. It can be used as a raw material for medicine, preparing stomach medicine and as a raw material for pesticides. |
| preparation | ① phenol is used as raw material to react with acrylonitrile to generate p-hydroxypropiononitrile, which is then hydrolyzed to obtain the product; ② using p-hydroxybenzaldehyde as raw material, Perkin reaction with acetic anhydride in the presence of sodium acetate to generate p-hydroxyacrylic acid, which can be prepared by hydrolysis. |
| Biological activity | Desaminotyrosine is a microbial-related metabolite that prevents influenza by expanding the type I interferon signal. |
| Uses | Used as a pharmaceutical intermediate Sensitive fluorescent substrate for horseradish peroxidase and other peroxidase. |
Last Update：2024-04-09 02:00:09
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