Santamarine

Base Information

• Chemical Name: Santamarine
• CAS No.: 4290-13-5
• Deprecated CAS: 6895-45-0,11016-81-2
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• UNII: 15D6KW291H
• DSSTox Substance ID: DTXSID70911513
• Nikkaji Number: J14.435E
• Wikidata: Q27089375
• Metabolomics Workbench ID: 50021
• ChEMBL ID: CHEMBL89311
• Mol file: 4290-13-5.mol

Synonyms:santamarin;santamarine

Chemical Property of Santamarine

Chemical Property:

• Vapor Pressure: 1.2E-08mmHg at 25°C
• Melting Point: 142 °C
• Refractive Index: 1.554
• Boiling Point: 415.6°Cat760mmHg
• PKA: 14.54±0.60(Predicted)
• Flash Point: 176.5°C
• PSA: 46.53000
• Density: 1.17g/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: 451

Purity/Quality:

99%, ^*data from raw suppliers

Santamarine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CCC(C2(C1C3C(CC2)C(=C)C(=O)O3)C)O
• Isomeric SMILES: CC1=CC[C@H]([C@]2([C@H]1[C@@H]3[C@@H](CC2)C(=C)C(=O)O3)C)O
• Uses: Santamarine is a sesquiterpene lactone shows anticancer properties by inhibiting proliferation and inducing apoptosis.

Technology Process of Santamarine

There total 14 articles about Santamarine 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: 100.0%

saussureamine D → santamarine (4290-13-5,16886-36-5,125290-03-1,11016-81-2,6895-45-0)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 12h;

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

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

Downstream raw materials:

santonin

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、 Matsuda, Hisashi,Kageura, Tadashi,Inoue, Yasunao,Morikawa, Toshio,Yoshikawa, Masayuki. "Absolute stereostructures and syntheses of saussureamines A, B, C, D and E, amino acid-sesquiterpene conjugates with gastroprotective effect, from the roots of Saussurea lappa". . p. 7763 - 7777. Retrieved 2007/10/03.