D-(-)-マンデル酸(611-71-2)

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D-(-)-マンデル酸 製品概要
化学名:D-(-)-マンデル酸
英語化学名:Mandelic acid
别名:(R)-(-)-AMYGDALIC ACID;(R)-ALPHA-HYDROXYPHENYLACETIC ACID;R-(-)-ALPHA-HYDROXYPHENYLACETIC ACID;D-A-HYDROXYPHENYLACETIC ACID;D-2-HYDROXY-PHENYLACETIC ACID;D-(-)-AMYGDALIC ACID;D-AMYGDALIC ACID;D-PHENYLGLYCOLIC ACID
CAS番号:611-71-2
分子式:C8H8O3
分子量:152.15
EINECS:210-276-6
カテゴリ情報:Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Miscellaneous;Chiral Compounds;chiral;Analytical Chemistry;Carboxylic Acids (Chiral);Chiral Building Blocks;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;Chiral Compound;FINE Chemical & INTERMEDIATES;Cosmetic;611-71-2
Mol File:611-71-2.mol
D-(-)-マンデル酸
D-(-)-マンデル酸 物理性質
融点 131-133 °C(lit.)
比旋光度 -150 º (c=2.5, H2O)
沸点 214.6°C (rough estimate)
比重(密度) 1.1677 (rough estimate)
屈折率 -153.5 ° (C=1, H2O)
闪点 >190℃
貯蔵温度 Store below +30°C.
溶解性109.8g/l soluble
外見 Crystalline Powder, Crystals or Flakes
酸解離定数(Pka)3.37(at 25℃)
White to slightly yellow-beige
PH3.34(1 mM solution);2.75(10 mM solution);2.22(100 mM solution);
光学活性 (optical activity)[α]25/D 151°, c = 1 in ethanol
水溶解度 It is partly soluble in water, freely soluble in isopropyl and ethyl alcohol.
Sensitive Light Sensitive
BRN 2691094
安定性:Stable, but light sensitive. Combustible. Incompatible with strong bases, strong oxidizing agents.
InChIKeyIWYDHOAUDWTVEP-SSDOTTSWSA-N
LogP0.550 (est)
CAS データベース611-71-2(CAS DataBase Reference)
EPAの化学物質情報Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.R)- (611-71-2)
安全性情報
主な危険性 Xi
Rフレーズ 41-36/37/38
Sフレーズ 22-24/25-36-26-39-37/39
WGK Germany 1
Hazard Note Irritant/Light Sensitive
TSCA Yes
HSコード 29181980
毒性LD50 orally in Rabbit: 5000 mg/kg
MSDS Information
ProviderLanguage
2-Phenylglycolic acid English
SigmaAldrich English
ACROS English
ALFA English
D-(-)-マンデル酸 Usage And Synthesis
外観白色,結晶~結晶性粉末
溶解性水及びエタノールに溶けやすい。
用途マンデル酸誘導体はいくつかのスキンケア日用品に含まれており、他の生体物質分子を産生する際の中間体であり、分析試薬や染料工業の前駆体として利用される。
用途アミン類の光学分割剤。
化学的特性white to light yellow crystal powde
使用(R)-(?)-Mandelic acid can be used:
  • As a chiral acid in the separation of diastereomeric salts for the synthesis of chiral pyridoindole based building block.
  • In the study of chiral acid selectivity of poly(3,4-ethylenedioxythiophene) (PEDOT) based chiral conducting?polymers.

使用(R)-(-)-Mandelic acid, is used as a antiseptic ingredient particularly against urinary tract infections.Mandelic acid and its derivatives are used to apply the dual activities as an antibacterial agent and as an antiaging agent. It is used as an intermediate for the synthesis of target molecules for other applications.
使用Antiseptic (urinary).
定義ChEBI: (R)-mandelic acid is the (R)-enantiomer of mandelic acid. It has a role as a human xenobiotic metabolite. It is a conjugate acid of a (R)-mandelate. It is an enantiomer of a (S)-mandelic acid.
Synthesis Reference(s)The Journal of Organic Chemistry, 33, p. 2565, 1968 DOI: 10.1021/jo01270a105
Synthetic Communications, 18, p. 2141, 1988 DOI: 10.1080/00397918808068285
一般的な説明(R)-(-)-Mandelic acid, a chiral resolving agent, is also used as a building block to synthesize pharmaceutical drugs such as penicillin and cephalosporin. It can be synthesized from (R,S)-mandelonitrile with high yield and enantioselectivity using nitrilase enzyme.
燃焼性と爆発性Non flammable
純化方法Purify the mandelic acids by recrystallisation from H2O, *C6H6 or CHCl3. [Roger J Chem Soc 2168 1932,Jamison & Turner J Chem Soc 611 1942.] They have solubilities in H2O of ca 11% at 25o. [Banks & Davies J Chem Soc 73 1938.] The S-benzylisothiuronium salts has m 180o (from H2O) and [] D 25 (+) and (-) 57o (c20, EtOH) [El Masri et al. Biochem J 68 199 1958]. [Beilstein 10 IV 564.]
Tags:611-71-2