2,3-Bis(1,3-benzodioxol-5-ylmethyl)butane-1,4-diol

Base Information

• Chemical Name: 2,3-Bis(1,3-benzodioxol-5-ylmethyl)butane-1,4-diol
• CAS No.: 24563-03-9
• Molecular Formula: C20H22 O6
• Molecular Weight: 358.391
• Hs Code.: 2932999099
• ChEMBL ID: CHEMBL1477391
• Wikidata: Q104169624
• Mol file: 24563-03-9.mol

Synonyms:MLS000863615;2,3-bis(1,3-benzodioxol-5-ylmethyl)butane-1,4-diol;MEGxp0_001537;CHEMBL1477391;SCHEMBL12488032;ACon1_001264;HMS2269J05;NCGC00169519-01;SMR000440737;BRD-A43097248-001-01-2;2,3-Bis(1,3-benzodioxol-5-ylmethyl)-1,4-butanediol, 9CI

Chemical Property of 2,3-Bis(1,3-benzodioxol-5-ylmethyl)butane-1,4-diol

Chemical Property:

• Vapor Pressure: 1.3E-14mmHg at 25°C
• Boiling Point: 586.8°Cat760mmHg
• Flash Point: 308.7°C
• PSA: 77.38000
• Density: 1.341g/cm³
• LogP: 2.14620
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 358.14163842
• Heavy Atom Count: 26
• Complexity: 406

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)CC(CO)C(CC3=CC4=C(C=C3)OCO4)CO

Technology Process of 2,3-Bis(1,3-benzodioxol-5-ylmethyl)butane-1,4-diol

There total 22 articles about 2,3-Bis(1,3-benzodioxol-5-ylmethyl)butane-1,4-diol 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: 90.0%

sesamin (133-03-9,133-04-0,133-05-1,551-30-4,607-80-7,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9) → dihydrocubebin (4621-68-5,24562-96-7,24563-03-9,103619-39-2)

Guidance literature:

With formic acid; ammonium formate; palladium 10% on activated carbon; In water; ethyl acetate; at 80 ℃; for 4h;

Reference yield: 48.0%

sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7) → (2S,3R,4R)-3-hydroxymethyl-4-(3,4-methylenedioxybenzyl)-2-(3,4-methylenedioxyphenyl)tetrahydrofuran (133644-85-6) + (-)-dihydrocubebin (24563-03-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1h;

DOI:10.1002/chir.23218

Reference yield:

(2R,3R)-1,4-bis((4R,5S)-3,4-dimethyl-2-oxo-5-phenylimidazolidinyl)-2,3-bis[(3,4-methylenedioxyphenyl)methyl]butane-1,4-dione (259540-41-5) → (-)-dihydrocubebin (24563-03-9)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo991317o

upstream raw materials:

sesamin

(2R,3R)-1,4-bis((4R,5S)-3,4-dimethyl-2-oxo-5-phenylimidazolidinyl)-2,3-bis[(3,4-methylenedioxyphenyl)methyl]butane-1,4-dione

(1R,2R)-1,2-bis[(3,4-methylenedioxyphenyl)methyl]ethane-1,2-dicarboxylic acid

vinyl acetate

Downstream raw materials:

(8R,8'R-)8,8'-bis-(3'4'-methylenedioxybenzyl)-tetrahydrofuran (-)-dehydroxycubebin

ariensin

Piperonylic acid

(-)-hinokinin

Refernces

HORSFIELDIN, A LIGNAN AND OTHER CONSTITUENTS FROM HORSFIELDIA IRYAGHEDHI

10.1016/0031-9422(82)83106-3

The study focuses on the phytochemical investigation of Horsfieldia iryaghedhi seeds, a plant indigenous to Sri Lanka. The researchers extracted and characterized several constituents from the hot methanol extract of the seeds, including a new lignan named horsfieldin, along with d-asarinin, (-)-dihydrocubebin, dodecanoylphloroglucinol, myristic acid, trimyristin, and sitosterol. The study provides detailed information on the structure elucidation and absolute configuration of the lignans, as well as discussing their chemotaxonomic significance. The findings contribute to the understanding of the chemical composition of H. iryaghedhi and its potential biological activities, as tetrahydrofuran lignans like horsfieldin have been shown to possess insecticidal and medicinal properties.

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