Goniodiol

Base Information

• Chemical Name: Goniodiol
• CAS No.: 96422-52-5
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252
• DSSTox Substance ID: DTXSID70242253
• Nikkaji Number: J1.781.968B
• Wikidata: Q72480804
• Metabolomics Workbench ID: 138798
• ChEMBL ID: CHEMBL490371
• Mol file: 96422-52-5.mol

Synonyms:goniodiol

Chemical Property of Goniodiol

Chemical Property:

• Vapor Pressure: 2.41E-10mmHg at 25°C
• Boiling Point: 488.2°C at 760 mmHg
• Flash Point: 192.1°C
• PSA: 66.76000
• Density: 1.306g/cm³
• LogP: 0.95260
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 234.08920892
• Heavy Atom Count: 17
• Complexity: 294

Purity/Quality:

> 95% ^*data from raw suppliers

Goniodiol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC(=O)OC1C(C(C2=CC=CC=C2)O)O
• Isomeric SMILES: C1C=CC(=O)O[C@H]1[C@@H]([C@@H](C2=CC=CC=C2)O)O

Technology Process of Goniodiol

There total 133 articles about Goniodiol 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: 98.0%

(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-5,6-dihydropyran-2-one (163630-06-6) → (+)-goniodiol (146236-73-9,96422-52-5)

Guidance literature:

With acetic acid; at 80 ℃; for 0.5h;

DOI:10.1039/b205230j

Reference yield: 97.0%

(R)-4-Benzenesulfonyl-6-((1R,2R)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one (214678-55-4) → (+)-goniodiol (146236-73-9,96422-52-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(98)01562-7

Reference yield: 97.0%

(R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one (194355-07-2) → (+)-goniodiol (146236-73-9,96422-52-5)

Guidance literature:

With titanium tetrachloride; In dichloromethane;

DOI:10.1021/jo970725u

upstream raw materials:

(R)-6-((R)-2-Hydroxy-1-methoxymethoxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one

(6R)-6-[(2S,3S)-3-phenyloxiran-2-yl]-5,6-dihydro-2H-pyran-2-one

(R)-4-Benzenesulfonyl-6-((1R,2R)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one

(R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one

Downstream raw materials:

7,8-di-O-acetyl-goniodiol

4-Nitro-benzoic acid (1S,2S)-2-benzyloxy-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenyl-ethyl ester

(1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one

(-)-(1R,5R,7S,8R)-8-benzyloxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

Refernces

Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e

10.1021/acs.jnatprod.6b00386

The study presents a protecting-group-free total synthesis of bioactive styryllactones, including (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (-)-parvistone D (4), and (+)-parvistone E (6), inspired by their proposed biosynthesis pathway. The synthesis starts from trans-cinnamaldehyde (10) and involves key steps such as stereoselective Maruoka allylation to obtain compound (S)-11, acrylation to form acrylate 12, ring-closing metathesis to produce a-pyrone 8, and stereoselective epoxidation to yield goniothalamin oxides 9a and 9b. The final products are obtained through regio- and stereoselective epoxide ring-opening reactions in aqueous media. The study achieves high overall yields (72-75%) in just five steps, supporting the proposed biosynthesis pathway and providing a concise and efficient route for synthesizing these natural products with potential biological activities.