reynosin

Base Information

• Chemical Name: reynosin
• CAS No.: 28254-53-7
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• UNII: N26569L9V4
• Nikkaji Number: J17.318E
• Wikidata: Q27105167
• Metabolomics Workbench ID: 52767
• ChEMBL ID: CHEMBL272178
• Mol file: 28254-53-7.mol

Synonyms:Eudesma-4(14),11(13)-dien-12-oicacid, 1b,6a-dihydroxy-, g-lactone (8CI); Naphtho[1,2-b]furan-2(3H)-one,decahydro-6-hydroxy-5a-methyl-3,9-bis(methylene)-, [3aS-(3aa,5ab,6b,9aa,9bb)]-; (+)-Reynosin; NSC 155623; Reinosin; Reynosin

Chemical Property of reynosin

Chemical Property:

• Vapor Pressure: 1.35E-08mmHg at 25°C
• Boiling Point: 414.3°Cat760mmHg
• Flash Point: 175.8°C
• PSA: 46.53000
• Density: 1.16g/cm³
• LogP: 2.21140
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 439

Purity/Quality:

99%, ^*data from raw suppliers

Reynosin ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1C(=C)CCC2O)OC(=O)C3=C
• Isomeric SMILES: C[C@@]12CC[C@@H]3[C@@H]([C@H]1C(=C)CC[C@H]2O)OC(=O)C3=C
• Uses: Reynosin is a sesquiterpene derived from Magnolia leaves which shows cytotoxic activity and production of melanin.

Technology Process of reynosin

There total 8 articles about reynosin 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: 70.0%

costunolide 1,10-epoxide (29484-23-9) → (+)-reynosin (29424-04-2,88153-66-6,125290-04-2,28254-53-7) + 11β,13-dihydroreynosin (32223-12-4)

Guidance literature:

With bis(cyclopentadienyl)titanium dichloride; manganese; In toluene; for 0.5h;

DOI:10.1021/jo016277e

Reference yield: 58.8%

costunolide (553-21-9) → santamarine (4290-13-5,16886-36-5,125290-03-1,11016-81-2,6895-45-0) + (+)-reynosin (29424-04-2,88153-66-6,125290-04-2,28254-53-7)

Guidance literature:

costunolide; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 24h;

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/cmdc.202000783

Reference yield: 47.0%

costunolide-1,10-epoxide (29484-23-9,68399-05-3,68399-06-4,72203-21-5) → santamarine (4290-13-5,16886-36-5,125290-03-1,11016-81-2,6895-45-0) + (+)-reynosin (29424-04-2,88153-66-6,125290-04-2,28254-53-7)

Guidance literature:

With boron trifluoride diethyl etherate; In benzene; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(00)00696-7

upstream raw materials:

gallicin

costunolide

costunolide-1,10-epoxide

costunolide 1,10-epoxide

Downstream raw materials:

Saussureamine E

Refernces

• 1、 Zorrilla, Jesús G.,Rial, Carlos,Varela, Rosa M.,Molinillo, José M.G.,Macías, Francisco A.. "Facile synthesis of anhydrojudaicin and 11,13-dehydroanhydrojudaicin, two eudesmanolide-skeleton lactones with potential allelopathic activity". . p. 229 - 236. Retrieved 2019/04/26.
• 2、 Barrero, Alejandro F.,Enrique Oltra,Cuerva, Juan M.,Rosales, Antonio. "Effects of solvents and water in Ti(III)-mediated radical cyclizations of epoxygermacrolides. Straightforward synthesis and absolute stereochemistry of (+)-3α-hydroxyreynosin and related eudesmanolides". . p. 2566 - 2571. Retrieved 2007/10/03.