D-ALPHA-AMINO-BETA-PHENYL-PROPIONIC ACID
(R)-Phenylalanine
CAS: 673-06-3
Molecular Formula: C9H11NO2
D-ALPHA-AMINO-BETA-PHENYL-PROPIONIC ACID - Names and Identifiers
| Name | (R)-Phenylalanine |
| Synonyms | D-PHE d-phe H-D-PHE-OH H-D-Phe-OH D-phenylalanie D-Phenylalanine D-PHENYLALANINE (R)-Phenylalanine D(+)-PHENYLALANINE d-alpha-aminohydrocinnamic acid D-alpha-aminohydrocinnamic acid D-2-AMINO-3-PHENYLPROPANOIC ACID D-beta-Phenyl-alpha-aminopropionic acid D-alpha-amino-beta-phenylpropionic acid D-beta-phenyl-alpha-aminopropionic acid D-ALPHA-AMINO-BETA-PHENYL-PROPIONIC ACID |
| CAS | 673-06-3 |
| EINECS | 211-603-5 |
| InChI | InChI=1/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m1/s1 |
| InChIKey | COLNVLDHVKWLRT-MRVPVSSYSA-N |
D-ALPHA-AMINO-BETA-PHENYL-PROPIONIC ACID - Physico-chemical Properties
| Molecular Formula | C9H11NO2 |
| Molar Mass | 165.19 |
| Density | 1.1603 (rough estimate) |
| Melting Point | 273-276°C(lit.) |
| Boling Point | 293.03°C (rough estimate) |
| Specific Rotation(α) | 33.5 º (c=2, H2O) |
| Water Solubility | 27 g/L (20 ºC) |
| Solubility | Soluble in water, slightly soluble in methanol and ethanol, insoluble in ether |
| Appearance | White crystalline powder |
| Color | White to off-white |
| Merck | 14,7271 |
| BRN | 2804068 |
| pKa | 2.2(at 25℃) |
| Storage Condition | Store at RT. |
| Stability | Stable. Incompatible with strong oxidizing agents, acids, bases. |
| Refractive Index | 34 ° (C=2, H2O) |
| MDL | MFCD00004270 |
| Physical and Chemical Properties | Melting point 273-276°C specific rotation 33.5 ° (c = 2, H2O) water-soluble 27g/L (20°C) |
| Use | Used as a pharmaceutical intermediate or API for the synthesis of nateglinide and other drugs |
D-ALPHA-AMINO-BETA-PHENYL-PROPIONIC ACID - Risk and Safety
| Risk Codes | 34 - Causes burns |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S27 - Take off immediately all contaminated clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | AY7533000 |
| TSCA | Yes |
| HS Code | 29224995 |
| Hazard Note | Irritant |
| Toxicity | TDLo orl-hmn: 500 mg/kg/5W-I:GIT JACTDZ 1(3),124,82 |
D-ALPHA-AMINO-BETA-PHENYL-PROPIONIC ACID - Reference
| Reference Show more | 1. Gan Hui Yu Huang Lu. Preparation and application of L-proline modified gold nanochannel [J]. Journal of Minjiang University, 2019, 40(02):101-105. 2. Xi, Y., du, Y., sun, X. et al. A monolithic capillium modified with a copolamer prepared from the ionic liquid 1-vinyl-3-octylimidazolium bromide and styles for chromatography of alkylbenzenes, polycyc aromatic pigments, and amino 3. [IF = 5.537] Yurong Ma et al."Pre-cut NaCl solution treatment effectively inhibited the browning of fresh-cut potato by influencing polyphenol oxidase activity and several free amino acids contents."Postharvest Biol Tec. 2021 Aug;178:111543 4. [IF=4.556] Dandan Zhao et al."Physico-chemical properties and free amino acids profiles of six wolfberry cultivars in Zhongning."J Food Compos Anal. 2020 May;88:103460 5. [IF=4.379] Feng Lin et al."Chemical profile changes during pile fermentation of Qingzhuan tea affect inhibition of α-amylase and lipase."Sci Rep-Uk. 2020 Feb;10(1):1-10 6. [IF=4.35] Xiaomei Dai et al."1-Methylcyclopropene Preserves the Quality of Chive (Allium schoenoprasum L.) Enhancing Its Antioxidant Capacities and Organosulfur Profile during Storage."Foods. 2021 Aug;10(8):1792 7. [IF=2.863] Qiang Wang et al."Effects of turmeric on reducing heterocyclic aromatic amines in Chinese tradition braised meat products and the underlying mechanism."Food Sci Nutr. 2021 Oct;9(10):5575-5582 |
D-ALPHA-AMINO-BETA-PHENYL-PROPIONIC ACID - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | phenylalanine scientific name α-amino-β-phenylpropionic acid, is a kind of α-amino acid, there are L-form, D-form and racemic DL-form, wherein L-form is one of the essential amino acids for human body. Phenylalanine is a new amino acid, which was first discovered by Schulze and Barbieri in the late Eighties of the ninth century, and was isolated from lupin seedlings. An empirical chemical formula for C9H11NO2 was proposed. Erlemeyer and Lipp successfully synthesized phenylalanine by chemical synthesis for the first time in 1882, but their spatial configuration was not explored. Further research on phenylalanine has been carried out since Fischer's accidental isolation of phenylalanine in the hydrolysis of casein with hydrochloric acid in 1901. D-phenylalanine is a kind of α-amino acid, the physical state is white powder or white crystalline solid at room temperature, melting point 283 ℃, isoelectric point (25 ℃) is 5.48,25 ° c in water solubility 27g/L, slightly soluble in methanol, ethanol, insoluble in ether, etc., specific rotation [α]25D = 34.5(c = 1.0,H2O). Like other D-amino acids, D-phenylalanine is a very important chiral intermediate in organic synthesis, new drug development and synthesis of polypeptide compounds, and because of the particularity of the structure and activity of D-phenylalanine amino acid, more and more people pay attention to it. |
| Use | for biochemical studies. The product is a drug intermediate, mainly used for the treatment and prevention of osteoporosis, cardiovascular, diabetes, arteriosclerosis and other diseases. D-Phenylalanine, the stereosomer of L-Phenylalanine (P319415) has been used in the synthesis of Schaeffer. They exhibit the ability to exhibit Mycobacterium tuberculosis type II dehydroquinase. used as a pharmaceutical intermediate or API for the synthesis of nateglinide and other drugs |
| production method | with DL-phenylalanine as raw material, acylation reaction with acetic anhydride, acetyl DL-phenylalanine, by acylase resolution, hydrochloric acid hydrolysis products. |
Last Update：2024-04-09 20:52:54
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