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(R)-(-)-扁桃酸

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    级别和纯度:
  • ≥99%
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M107076-25g
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M107076-100g
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M107076-250g
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M107076-500g
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M107076-2.5kg
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M107076-5kg
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基本描述

别名 扁桃酸
英文别名 (-)-Mandelic acid | mandelic_acid | s9003 | 1mcz | D-(-)-Mandelic acid, puriss., >=99.0% (T) | NCGC00166022-01 | (-)-(R)-Mandelate | D70151 | (-)-(R) alpha-hydroxybenzeneacetic acid | DTXSID4046523 | SR-01000946767-1 | (-)-alpha-Hydroxyphenylacetic acid |
规格或纯度 ≥99%
英文名称 (R)-(-)-Mandelic acid
应用 分析碱的试剂，经由酯分析醇， 经由二氧戊环立体选择性的α-烷基化分析 R-(-)-Mandelic Acid is a synthetic intermediate commonly used for pharmaceutical synthesis. ;(R)-(-)-Mandelic acid has been used in studies to assess its ability to undergo spontaneous oscillatory chiral conversion and spontaneous condensation to form polymandelic acid.
储存温度 避光
运输条件 常规运输
产品介绍

水中溶解度: 100 g/l (25°C),溶于乙醇和醚,（R）-（-）-扁桃酸，一种手性拆分剂， 也被用作合成药物（如青霉素和头孢菌素）的结构单元。通过腈水解酶，它可以从（合成）R，S）-甘露腈进行高产率和对映选择性的合成。分析碱的试剂，经由酯分析醇， 经由二氧戊环立体选择性的α-烷基化分析 R-(-)-Mandelic Acid is a synthetic intermediate commonly used for pharmaceutical synthesis. ;(R)-(-)-Mandelic acid has been used in studies to assess its ability to undergo spontaneous oscillatory chiral conversion and spontaneous condensation to form polymandelic acid.

(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.
R-(-)-Mandelic Acid is a synthetic intermediate commonly used for pharmaceutical synthesis. ;(R)-(-)-Mandelic acid has been used in studies to assess its ability to undergo spontaneous oscillatory chiral conversion and spontaneous condensation to form polymandelic acid.
纯度 ≥99%

关联靶点（人）

PTPN7 Tchem Protein-tyrosine phosphatase LC-PTP (886 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GAPDH Tchem Glyceraldehyde-3-phosphate dehydrogenase liver (1284 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

关联靶点（其它种属）

Ptpn1 Protein-tyrosine phosphatase 1B (270 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
mdlA Mandelate racemase (27 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Dusp6 Dual specificity protein phosphatase 6 (459 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SARS-CoV-2 (38078 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

作用机制

作用机制 Action Type target ID Target Name Target Type Target Organism Binding Site Name 参考文献

名称和识别符

PubChem SID 488181475
EC号 210-276-6
分子类型 小分子
IIUPAC Name (2R)-2-hydroxy-2-phenylacetic acid
INCHI 1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1
InChi Key IWYDHOAUDWTVEP-SSDOTTSWSA-N
Smiles C1=CC=C(C=C1)C(C(=O)O)O
Isomeric SMILES C1=CC=C(C=C1)[C@H](C(=O)O)O
分子量 152.15
Beilstein号 2691094
Reaxy-Rn 510011
Reaxys-RN link address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=510011&ln=

化学和物理性质

溶解性 It is partly soluble in water, freely soluble in isopropyl and ethyl alcohol.
密度 1.321
敏感性 对光敏感
比旋光度 -150.0 to -157.0 deg(C=1, H2O)
闪点(℉) >374 °F
闪点(℃) >190 °C
熔点 131-135°C
分子量 152.150 g/mol
XLogP3 0.600
氢键供体数Hydrogen Bond Donor Count 2
氢键受体数Hydrogen Bond Acceptor Count 3
可旋转键计数Rotatable Bond Count 2
精确质量Exact Mass 152.047 Da
单同位素质量Monoisotopic Mass 152.047 Da
拓扑极表面积Topological Polar Surface Area 57.500 Ų
重原子数Heavy Atom Count 11
形式电荷Formal Charge 0
复杂度Complexity 138.000
同位素原子数Isotope Atom Count 0
定义的原子立体中心计数Defined Atom Stereocenter Count 1
未定义的原子立体中心计数Undefined Atom Stereocenter Count 0
定义的键立体中心计数Defined Bond Stereocenter Count 0
未定义的键立体中心计数Undefined Bond Stereocenter Count 0
所有立体化学键的总数The total count of all stereochemical bonds 0
共价键合单元计数Covalently-Bonded Unit Count 1

安全和危险性（GHS）

象形图 GHS05
信号词 危险
WGK Germany 1
个人防护装备 Eyeshields,Gloves,type N95 (US),type P1 (EN143) respirator filter

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F2110259 分析证书 M107076
H2514054 分析证书 M107076
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引用文献

1. Jennifer R Bourque,Rodney K M Burley,Stephen L Bearne.  (2006-10-24)  Intermediate analogue inhibitors of mandelate racemase: N-Hydroxyformanilide and cupferron..  Bioorganic & medicinal chemistry letters,  17  ((1)): (105-108).  [PMID:17055725]
2. Ya-Ping Xue,Sai-Zhen Xu,Zhi-Qiang Liu,Yu-Guo Zheng,Yin-Chu Shen.  (2010-07-20)  Enantioselective biocatalytic hydrolysis of (R,S)-mandelonitrile for production of (R)-(-)-mandelic acid by a newly isolated mutant strain..  Journal of industrial microbiology & biotechnology,  38  ((2)): (337-345).  [PMID:20640871]
3. Yubo Wu,Huimin Guo,Tony D James,Jianzhang Zhao.  (2011-05-31)  Enantioselective recognition of mandelic acid by a 3,6-dithiophen-2-yl-9H-carbazole-based chiral fluorescent bisboronic acid sensor..  The Journal of organic chemistry,  76  ((14)): (5685-5695).  [PMID:21619028]
4. Zhoutong Sun,Yuanyuan Ning,Lixia Liu,Yingmiao Liu,Bingbing Sun,Weihong Jiang,Chen Yang,Sheng Yang.  (2011-09-14)  Metabolic engineering of the L-phenylalanine pathway in Escherichia coli for the production of S- or R-mandelic acid..  Microbial cell factories,  10  (71-71).  [PMID:21910908]
5. Ivo B Rietveld,Maria Barrio,Josep-Lluis Tamarit,Bernard Do,René Céolin.  (2011-11-04)  Enantiomer resolution by pressure increase: inferences from experimental and topological results for the binary enantiomer system (R)- and (S)-mandelic acid..  The journal of physical chemistry. B,  115  ((49)): (14698-14703).  [PMID:22047025]
6. Yingzi Fu,Qiao Chen,Juan Zhou,Qian Han,Yonghua Wang.  (2011-11-08)  Enantioselective recognition of mandelic acid based on γ-globulin modified glassy carbon electrode..  Analytical biochemistry,  421  ((1)): (103-107).  [PMID:22056409]
7. Karel Hernandez,Eduardo Garcia-Verdugo,Raul Porcar,Roberto Fernandez-Lafuente.  (2011-11-25)  Hydrolysis of triacetin catalyzed by immobilized lipases: effect of the immobilization protocol and experimental conditions on diacetin yield..  Enzyme and microbial technology,  48  ((6-7)): (510-517).  [PMID:22113024]
8. Ling-Bo Gao,Jin-Zhao Wang,Tong-Wei Yao,Su Zeng.  (2011-12-06)  Study on the metabolic mechanism of chiral inversion of S-mandelic acid in vitro..  Chirality,  24  ((1)): (86-95).  [PMID:22139827]
9. Quan He,Sohrab Rohani,Jesse Zhu,Hassan Gomaa.  (2011-12-17)  Resolution of sertraline with (R)-mandelic acid: chiral discrimination mechanism study..  Chirality,  24  ((2)): (119-128).  [PMID:22173987]
10. Selahattin Bozkurt,Mustafa Yilmaz,Abdulkadir Sirit.  (2011-12-20)  Chiral calix[4]arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid..  Chirality,  24  ((2)): (129-136).  [PMID:22180195]
11. Liang Jin,Pei-ying Hao,Sheng-zhang Dong,Ya-lin Bian,Xiao-ping Yu.  (2011-12-24)  Antifeedant and insecticidal effects of mandelic acid on the brown planthopper Nilaparvata lugens Stål..  Zeitschrift fur Naturforschung. C, Journal of biosciences,  66  ((9-10)): (499-506).  [PMID:22191216]
12. Tsuyoshi Mita,Masumi Sugawara,Hiroyuki Hasegawa,Yoshihiro Sato.  (2012-02-01)  Synthesis of arylglycine and mandelic acid derivatives through carboxylations of α-amido and α-acetoxy stannanes with carbon dioxide..  The Journal of organic chemistry,  77  ((5)): (2159-2168).  [PMID:22288831]
13. Frédéric Cosnier,Hervé Nunge,Benoît Cossec,Laurent Gaté.  (2012-04-12)  Simultaneous determination of aromatic acid metabolites of styrene and styrene-oxide in rat urine by gas chromatography-flame ionization detection..  Journal of analytical toxicology,  36  ((5)): (312-318).  [PMID:22492963]
14. P G Jaison,Vijay M Telmore,Pranaw Kumar,Suresh K Aggarwal.  (2012-05-16)  Determination of uranium in seawater samples by liquid chromatography using mandelic acid as a complexing agent..  Journal of chromatographic science,  49  ((9)): (657-664).  [PMID:22586240]
15. Carla Costa,Solange Costa,Susana Silva,Patrícia Coelho,Mónica Botelho,Jorge Gaspar,José Rueff,Blanca Laffon,João Paulo Teixeira.  (2012-07-14)  DNA damage and susceptibility assessment in industrial workers exposed to styrene..  Journal of toxicology and environmental health. Part A,  75  ((13-15)): (735-746).  [PMID:22788361]
16. Shimin Mao,Yan Zhang,Sohrab Rohani,Ajay K Ray.  (2012-07-19)  Chromatographic resolution and isotherm determination of (R,S)-mandelic acid on Chiralcel-OD column..  Journal of separation science,  35  ((17)): (2273-2281).  [PMID:22807393]
17. Elena Ilyes,Mihaela Florea,Augustin M Madalan,Ionel Haiduc,Vasile I Parvulescu,Marius Andruh.  (2012-07-27)  A robust metal-organic framework constructed from alkoxo-bridged binuclear nodes and hexamethylenetetramine spacers: crystal structure and sorption studies..  Inorganic chemistry,  51  ((15)): (7954-7956).  [PMID:22830491]
18. Jiao-Jiao Shangguan,Li-Qiang Fan,Xin Ju,Qing-Qing Zhu,Fu-Jun Wang,Jian Zhao,Jian-He Xu.  (2012-10-12)  Expression and characterization of a novel enantioselective lipase from Aspergillus fumigatus..  Applied biochemistry and biotechnology,  168  ((7)): (1820-1833).  [PMID:23054817]
19. Giovanna Tranfo,Monica Gherardi,E Paci,Mariapia Gatto,A Gordiani,Lidia Caporossi,Silvia Capanna,Renata Sisto,B Papaleo,Carla Fiumalbi,Patrizia Garofani.  (2012-10-20)  Occupational exposure to styrene in the fibreglass reinforced plastic industry: comparison between two different manufacturing processes..  La Medicina del lavoro,  103  ((5)): (402-412).  [PMID:23077800]
20. Benedict T Green,Stephen T Lee,Kevin D Welch,James A Pfister,Kip E Panter.  (2012-10-23)  Fetal muscle-type nicotinic acetylcholine receptor activation in TE-671 cells and inhibition of fetal movement in a day 40 pregnant goat model by optical isomers of the piperidine alkaloid coniine..  The Journal of pharmacology and experimental therapeutics,  344  ((1)): (295-307).  [PMID:23086230]
21. Tianyi Jiang,Chao Gao,Peipei Dou,Cuiqing Ma,Jian Kong,Ping Xu.  (2012-11-28)  Rationally re-designed mutation of NAD-independent L-lactate dehydrogenase: high optical resolution of racemic mandelic acid by the engineered Escherichia coli..  Microbial cell factories,  11  (151-151).  [PMID:23176608]
22. Mária Poláková,Zdenka Krajcovicová,Vladimír Melus,Mária Stefkovicová,Margaréta Sulcová.  (2013-01-05)  Study of urinary concentrations of mandelic acid in employees exposed to styrene..  Central European journal of public health,  20  ((3)): (226-232).  [PMID:23285526]
23. M Monier,A El-Mekabaty.  (2013-01-30)  Preparation of molecularly imprinted resin based on chitosan for chiral recognition of S-mandelic acid..  International journal of biological macromolecules,  55  (207-213).  [PMID:23357795]
24. Mark B Taylor,Jamal S Yanaki,David O Draper,Joe C Shurtz,Mark Coglianese.  (2013-02-05)  Successful short-term and long-term treatment of melasma and postinflammatory hyperpigmentation using vitamin C with a full-face iontophoresis mask and a mandelic/malic acid skin care regimen..  Journal of drugs in dermatology : JDD,  12  ((1)): (45-50).  [PMID:23377327]
25. Hui-Shi Guo,Xiao-Yu Han,Woo-Sik Kim.  (2013-03-02)  Self-assembly of L-cysteine for chiral recognition of mandelic acid in gas phase..  Journal of nanoscience and nanotechnology,  12  ((12)): (8874-8878).  [PMID:23447931]
26. Lana E Greene,J Stuart Grossert,Robert L White.  (2013-03-16)  Correlations of ion structure with multiple fragmentation pathways arising from collision-induced dissociations of selected α-hydroxycarboxylic acid anions..  Journal of mass spectrometry : JMS,  48  ((3)): (312-320).  [PMID:23494786]
27. Qiu-Yun Wang,Ya-Jin Xiong,Bao-Zhu Lu,Jun Fan,Sheng-Run Zheng,Wei-Guang Zhang.  (2013-08-06)  Effect of chromatographic conditions on enantioseparation of bovine serum albumin chiral stationary phase in HPLC and thermodynamic studies..  Chirality,  25  ((9)): (487-492).  [PMID:23913549]
28. Hiroaki Shitara,Toshiki Shintani,Koichi Kodama,Takuji Hirose.  (2013-08-09)  Solvent-induced reversed stereoselectivity in reciprocal resolutions of mandelic acid and erythro-2-amino-1,2-diphenylethanol..  The Journal of organic chemistry,  78  ((18)): (9309-9316).  [PMID:23924430]
29. Jarosław M Granda,Janusz Jurczak.  (2013-08-31)  Sweet anion receptors: recognition of chiral carboxylate anions by D-glucuronic-acid-decorated diindolylmethane..  Organic letters,  15  ((18)): (4730-4733).  [PMID:23988260]
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31. Chao Ma,Xiao-Lin Xu,Ping Ai,Sheng-Ming Xie,Ying-Chun Lv,Hai-Qin Shan,Li-Ming Yuan.  (2011-04-14)  Chiral separation of D,L-mandelic acid through cellulose membranes..  Chirality,  23  ((5)): (379-382).  [PMID:21488105]
32. Tiantian Wan, Zulei Zhang, Hailong Wang, Yiwen Yang, Hanxing Yang, Jian Zhang, Yanbo Zeng, Lei Li, Jinchun Li.  (2023)  Rapid and highly selective detection of chlorogenic acid in fruit samples by Fe3O4@SiO2@PIL with boron affinity via a fluorescence enhanced strategy.  NEW JOURNAL OF CHEMISTRY,  47  (2): (828-837).  [10.1039/D2NJ04750K]
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