acerogenin A

Base Information

• Chemical Name: acerogenin A
• CAS No.: 60503-28-8
• Molecular Formula: C19H22O3
• Molecular Weight: 298.38
• ChEMBL ID: CHEMBL516665
• DSSTox Substance ID: DTXSID801143415
• Metabolomics Workbench ID: 141429
• Nikkaji Number: J17.926D
• Wikidata: Q105128190
• Mol file: 60503-28-8.mol

Synonyms:acerogenin A

Chemical Property of acerogenin A

Chemical Property:

• PSA: 49.69000
• LogP: 4.20440
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 298.15689456
• Heavy Atom Count: 22
• Complexity: 325

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2=CC(=C(C=C2)O)OC3=CC=C(CCC(C1)O)C=C3
• Isomeric SMILES: C1CCC2=CC(=C(C=C2)O)OC3=CC=C(CC[C@@H](C1)O)C=C3

Technology Process of acerogenin A

There total 5 articles about acerogenin A 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: 42.0%

aceroketoside → (12R)-2-oxatricyclo[13.2.2.13,7]icosa-3,5,7(20),15,17,18-hexaene-4,12-diol (60503-28-8)

Guidance literature:

With Penicillium decumbens; In acetate buffer; at 38 ℃; for 96h; pH=4.8;

DOI:10.1021/np020351m

Reference yield:

acerogenin A 11-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranoside (74390-29-7) → acerogenin A (60503-28-8)

Guidance literature:

With sulfuric acid; for 1h; Heating;

Reference yield:

aceroside I (65987-95-3) → (12R)-2-oxatricyclo[13.2.2.13,7]icosa-3,5,7(20),15,17,18-hexaene-4,12-diol (60503-28-8)

Guidance literature:

With hydrogenchloride; methanol; for 2h; Reflux;

DOI:10.1002/cbdv.201200024

upstream raw materials:

acerogenin A 11-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranoside

aceroside I

Downstream raw materials:

acerogenin A dibenzoate

C₃₃H₂₈Cl₂O₅

(12R)-2-oxatricyclo[13.2.2.13,7]icosa-3,5,7⁽²⁰⁾,15,17,18-hexaene-4,12-diyl bis[(2E)-3 phenylprop-2-enoate]

acerogenin A benzyl ether

Refernces

• 1、 Akihisa, Toshihiro,Takeda, Ayano,Akazawa, Hiroyuki,Kikuchi, Takashi,Yokokawa, Satoru,Ukiya, Motohiko,Fukatsu, Makoto,Watanabe, Kensuke. "Melanogenesis-inhibitory and cytotoxic activities of diarylheptanoids from acer nikoense bark and their derivatives". . p. 1475 - 1489. Retrieved 2012/10/30.
• 2、 Nagai,Kubo,Fujita,et al.. "Studies on the constituents of aceraceae plants. II. Structure of aceroside I, a glucoside of a novel cyclic diarylheptanoid from Acer nikoense Maxim". . p. 2805 - 2810. Retrieved 2007/10/10.