Arctigenin

Base Information

• Chemical Name: Arctigenin
• CAS No.: 7770-78-7
• Molecular Formula: C₂₁H₂₄O₆
• Molecular Weight: 372.418
• UNII: 2FD8L150E7,U76MR9VS6M
• DSSTox Substance ID: DTXSID60998919
• Nikkaji Number: J16.086E
• Wikipedia: Arctigenin
• Wikidata: Q4787603
• NCI Thesaurus Code: C93251
• Pharos Ligand ID: J158CXX82XR3
• Metabolomics Workbench ID: 44200
• ChEMBL ID: CHEMBL435734
• Mol file: 7770-78-7.mol

Synonyms:2(3H)-furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R-trans)-;arctigenin

Chemical Property of Arctigenin

Chemical Property:

• Vapor Pressure: 1.85E-13mmHg at 25°C
• Melting Point: 98.0 to 102.0 °C
• Refractive Index: 1.576
• Boiling Point: 567 °C at 760 mmHg
• PKA: 10.03±0.20(Predicted)
• Flash Point: 198.8 °C
• PSA: 74.22000
• Density: 1.227 g/cm³
• LogP: 2.99240
• Storage Temp.: −20°C
• Solubility.: DMSO: 34 mg/mL with heating and sonicating, soluble
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 372.15728848
• Heavy Atom Count: 27
• Complexity: 483

Purity/Quality:

Arctigenin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)C[C@H]2COC(=O)[C@@H]2CC3=CC(=C(C=C3)O)OC)OC
• Recent ClinicalTrials: The Safety and Intake Rate of a Natural Compound Arctigenin in Healthy Men
• Uses: Arctigenin is a plant ligan associated with anticancer and antioxidant properties.

Technology Process of Arctigenin

There total 39 articles about Arctigenin 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: 80.0%

(7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone (74861-40-8) → Arctigenin (26687-82-1,81446-30-2,84413-77-4,87678-74-8,87678-75-9,144901-91-7,7770-78-7)

Guidance literature:

With perchloric acid; hydrogen; palladium on activated charcoal; In ethanol; for 48h; under 3040 Torr;

DOI:10.1021/ol049878b

Reference yield: 63.0%

(3R,4R)-3-[(3-methoxy-4-benzyloxyphenyl)methyl]-4-[(3,4-dimethoxyphenyl)methyl] dihydro-2-(3H)-furanone (123251-05-8) → Arctigenin (26687-82-1,81446-30-2,84413-77-4,87678-74-8,87678-75-9,144901-91-7,7770-78-7)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2020.127191

Reference yield: 21.0%

arctiin (20362-31-6) → diarctigenin + Arctigenin (26687-82-1,81446-30-2,84413-77-4,87678-74-8,87678-75-9,144901-91-7,7770-78-7)

Guidance literature:

With Rhizoctonia solani Kühn AG-4; at 27 ℃; for 168h; Mechanism; Enzymatic reaction;

DOI:10.1016/j.tetlet.2013.10.057

upstream raw materials:

3-methoxy-4-(phenylmethoxy)benzaldehyde

4-[(3,4-dimethoxyphenyl)methyl]dihydrofuran-2-one

(3R,4R)-3-[(3-methoxy-4-benzyloxyphenyl)methyl]-4-[(3,4-dimethoxyphenyl)methyl] dihydro-2-(3H)-furanone

(8S,8'R)-4-hydroxy-3,3',4'-trimethoxylignano-9,9'-lactone

Downstream raw materials:

trans-2-(4''-hydroxy-3''-methoxybenzyl)-3-(3',4'-dimethoxybenzyl)butyrolactone

rel(1a,12aS_a,6R,7R)-11-hydroxy-6-hydroxymethyl-2,3,10-trimethoxy-5,6,7,8-tetrahydrodibenzo<1a,4a:8a,12a>cyclooctene-7-carboxylic acid lactone

C₂₁H₂₂O₆

dimethylmatairesinol

Refernces

• 1、 Nishi, Kosuke,Nishimoto, Asuka,Nishiwaki, Hisashi,Sugahara, Takuya,Yamauchi, Satoshi. "Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring". supporting information. . Retrieved 2020/04/29.
• 2、 Xin, Hong,Xia, Yang-Liu,Hou, Jie,Wang, Ping,He, Wei,Yang, Ling,Ge, Guang-Bo,Xu, Wei. "Identification and characterization of human UDP-glucuronosyltransferases responsible for the in-vitro glucuronidation of arctigenin". . p. 1673 - 1681. Retrieved 2016/01/26.