Prunasin

Base Information

• Chemical Name: Prunasin
• CAS No.: 99-18-3
• Deprecated CAS: 1300-20-5
• Molecular Formula: C14H17 N O6
• Molecular Weight: 295.292
• European Community (EC) Number: 202-738-0
• UNII: 14W4BPM5FB
• DSSTox Substance ID: DTXSID001018995
• Nikkaji Number: J113.483C
• Wikipedia: Prunasin
• Wikidata: Q7253027
• Metabolomics Workbench ID: 46761
• ChEMBL ID: CHEMBL1778417
• Mol file: 99-18-3.mol

Synonyms:(R)-prunasin;benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-;mandelonitrile-beta-glucoside;prulaurasin;prunasin;prunasin, (R)-isomer;prunasine

Chemical Property of Prunasin

Chemical Property:

• Melting Point: 138-148°C
• Boiling Point: 527°Cat760mmHg
• PKA: 12.71±0.70(Predicted)
• Flash Point: 272.5°C
• PSA: 123.17000
• Density: 1.45g/cm³
• LogP: -0.93222
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 295.10558726
• Heavy Atom Count: 21
• Complexity: 377

Purity/Quality:

98%min ^*data from raw suppliers

(R)-Prunasin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 36/37/38-25-60
• Safety Statements: 26-36/37/39-61-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Description: (R)-Prunasin is a cyanogenic glucoside that is the precursor to amygdalin, a bitter component found in species of the genera Prunus and Olinia. It can be degraded to hydrogen cyanide, glucose, and benzaldehyde by the action of prunasin hydrolase and mandelonitrile lyase and possesses inhibitory effects on plant growth. (R)-Prunasin reportedly inhibits rat DNA polymerase β, which performs base excision repair required for DNA maintenance and replication, with an IC50 value of 98 μM.
• Uses: Used in the synthesis of cyanogen glycoside. A component of antiperspirants, deodorants, body soaps, shampoos, hair rinses, and hair

Technology Process of Prunasin

There total 14 articles about Prunasin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

(2R)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylacetonitrile (60981-47-7) → prunasin (99-18-3)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; diethyl ether; for 14h; Ambient temperature;

DOI:10.1271/bbb.62.453

Reference yield:

amygdalin (29883-15-6,672-72-0) → (R)-Mandelonitrile (10020-96-9) + benzaldehyde (100-52-7) + prunasin (99-18-3)

Guidance literature:

With β-glucosidase; for 0.0833333h; Enzymatic reaction;

DOI:10.1021/acs.jafc.8b03686

Reference yield:

phenylhydrazine (100-63-0) + (R)-mandelonitrile β-sophoroside → glucosazone (534-97-4) + prunasin (99-18-3)

Guidance literature:

With hydrogenchloride; Multistep reaction; 1.) 100 deg C, 1 h;

DOI:10.1016/S0031-9422(00)83060-5

upstream raw materials:

phenylhydrazine

(2R)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylacetonitrile

(2R)-mandelamide

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

Downstream raw materials:

(2R)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylacetonitrile

benzaldehyde

MANDELIC ACID

(R)-α-(β-D-glucopyranosyloxy)phenylacetamide

Refernces

• 1、 Zhang, Congcong,Zhang, Dingqi,Wang, Yongli,Zhang, Linzhang,Qi, Shenglan,Fang, Qinqin,Xu, Ying,Chen, Jiamei,Cheng, Xuemei,Liu, Ping,Wang, Changhong,Liu, Wei. "Pharmacokinetics and anti-liver fibrosis characteristics of amygdalin: Key role of the deglycosylated metabolite prunasin". . . Retrieved 2022/03/07.
• 2、 Moller, Birger L.,Olsen, Carl E.,Motawia, Mohammed S.. "General and Stereocontrolled Approach to the Chemical Synthesis of Naturally Occurring Cyanogenic Glucosides". supporting information. p. 1198 - 1202. Retrieved 2016/05/24.