Santonin

Base Information

• Chemical Name: Santonin
• CAS No.: 481-06-1
• Deprecated CAS: 881738-49-4
• Molecular Formula: C15H18 O3
• Molecular Weight: 246.306
• European Community (EC) Number: 207-560-7
• NSC Number: 4900
• UNII: 1VL8J38ERO
• DSSTox Substance ID: DTXSID7045312
• Nikkaji Number: J6.172G
• Wikipedia: Santonin
• Wikidata: Q413166
• NCI Thesaurus Code: C87627
• Metabolomics Workbench ID: 28280
• ChEMBL ID: CHEMBL259254
• Mol file: 481-06-1.mol

Synonyms:Santonin

Chemical Property of Santonin

Chemical Property:

• Vapor Pressure: 2.24E-07mmHg at 25°C
• Melting Point: 172-173 °C(lit.)
• Refractive Index: -172.5 ° (C=2, CHCl3)
• Boiling Point: 423.4°Cat760mmHg
• Flash Point: 189.7°C
• PSA: 43.37000
• Density: 1.18g/cm³
• LogP: 2.41960
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly)
• Water Solubility.: 0.2g/L(17.5 oC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 246.125594432
• Heavy Atom Count: 18
• Complexity: 500

Purity/Quality:

98% ^*data from raw suppliers

(-)-Santonin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic by ingestion, affects color vision.
• Hazard Codes: Xn,Xi,T+
• Statements: 22-36/37/38-26/27/28
• Safety Statements: 22-24/25-45-37-36-28-26

MSDS Files:

Useful:

• Canonical SMILES: CC1C2CCC3(C=CC(=O)C(=C3C2OC1=O)C)C
• Isomeric SMILES: C[C@H]1[C@@H]2CC[C@]3(C=CC(=O)C(=C3[C@H]2OC1=O)C)C
• Description: Santonin is a lactone compound extracted from the flower bud of Artemisia cina Berg in Compositae, crown daisy chrysanthemum or other plants in Artemisia. It has been recorded in ancient China . Its English name is santonica wormseed, Chinese alias is ‘quhaosu’ and Latin name is Seriphidium cinum (Berg ex Poljak.) Pol-jak. . Santonica wormseed, a variant name for Artemisia cina Berg, is the leaf and anthotaxy of Artemisia cina Berg in sagebrush plants in Compositae. There are more than 100 plus in sagebrush, in which about 30 plus live in China, and parts of them can be used medicinally.Santonica wormseed, used as raw material to extract and manufacture santonin, lives in cold, dry sandy loam. The place of origin is the Southern Central Asia in the former Soviet Union. China introduced the earliest cultivation in Xinjiang, and now it is introduced and cultivated in the North, Northeast and Northwest China. Santonica wormseed mainly contains hispidulin, quercetin and caffeic acid, and its flower contains 1–3.5% α-santonin, 1–3% artemisinin and volatile oil (mainly is 1, 8-cineole) and so on. Leaf also contains a small amount of α-santonin. In addition, it also contains β-cintonin, 3,4,5,7-tetrahydroxy-3-methoxyflavone7- glucoside and aglucone.
• Physical properties: Appearance: a colourless prism crystal or white crystalline powder, odourless, a little taste bitter and turning yellow in the sunlight. Solubility: hardly soluble in water, sparingly soluble in ethanol, freely soluble in boiling ethanol and chloroform and slightly soluble in diethyl ether. Melting point: 170–174 °C. Specific optical rotation: ?170 to ?175°, determined on 1% ethanol solution at 25 °C.Santonin is a kind of ketolide with two double bonds. It forms a salt by the ring opening when dissolving in alkaline solutions and reforms ketolide by acidification.
• Uses: anthelmintic (-)-Santonin is a sesquiterpene lactone derivative which acts as an anti-pyretic agent when tested with subjects antagonized by haloperidol. Causes a decrease in temperature of mammals. (?)-α-Santonin has been used as a eudesmane-type sesquiterpene to study its effects on impairment of 231MFP breast cancer cell survival.
• Indications: As a kind of deworming drug, santonin was effective for the treatment of human roundworm infection, but it is no longer in use at present because of the development of more effective medicines.
• Clinical Use: Santonin has been used for a long time as a kind of deworming drug. Its mechanism is between inhibitory effect on γ-GABA and excitatory effect of cholinergic func tion. It also acts on the human central nervous system and can cause some adverse effects, such as dizziness, leipopsychia, headache, epilepsy, xanthopsia, paresthesia and so onSantonin is easily dissolved and absorbed in the intestine due to alkaline intesti nal fluid and solvent effect of bile salts. Especially, it can cause severe toxic reaction more easily for increasing absorption because intake of fatty food promotes bile production, secretion and release.Santonin has obvious central nervous system toxicity. A small amount can cause colour deficiency, and a large amount can cause epileptiform, excessive excitement turning into severe repression and even coma. Santonin is a highly toxic substance. Children’s lethal dose is 0.15 g; adults’ lethal dose is about 1 g. Santonin has already been phased out for the toxicity.

Technology Process of Santonin

There total 136 articles about Santonin 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: 68.0%

(6α,11β)-eudesm-2,4-dien-13,6-olide (98612-83-0) → (2α, 5α, 6β, 11α)-2,5-peroxyeudesm-3-en-13,6-olide (98612-84-1) + santonin (481-06-1)

Guidance literature:

With Eosin Y; oxygen; abs. ethanol, irradiation, 15 deg C, 9 h;

Reference yield: 56.0%

(11S)-4α-bromo-3-oxoeudesm-1-eno-12,6α-lactone (539802-40-9) → (11S)-3-oxoeudesma-1,4(15)-dieno-12,6α-lactone (75683-62-4) + santonin (481-06-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 25.5h;

DOI:10.1021/np0205250

Reference yield: 46.0%

(11S)-3-oxoeudesma-1,4(15)-dieno-12,6α-lactone (75683-62-4) → santonin (481-06-1)

Guidance literature:

With lithium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 2h;

DOI:10.1039/c39800000495

upstream raw materials:

2,4,6-trimethyl-pyridine

(-)(11Ξ)-6α-hydroxy-11-methyl-3-oxo-eudesma-1,4-diene-12,13-dioic acid-lactone

6-hydroxy-3-oxo-eudesma-1,4-dien-12-oic acid

pyridine

Downstream raw materials:

(3aS)-3c,6,6a-trimethyl-(3ar,6at,9bt)-3a,4,5,6,6a,9b-hexahydro-3H-6c,9ac-cyclo-azuleno[4,5-b]furan-2,7-dione

(11S)-4,5-epoxy-6α-hydroxy-3-oxo-eudesm-1-en-12-oic acid-lactone

3,5a,9-[trimethyl-2-oxo-2,4,5,5a,6,7-hexahydronaphtho[1,2-b]furan-8-yl] acetate

α-desmotroposantonin acetate

Refernces

• 1、 Inayama, Seiichi,Shimizu, Nobuko,Shibata, Tetuichi,Hori, Hitoshi,Iitaka, Yoichi. "Unusual Bromination of Tetrahydro-(-)-α-santonins and New Santonin Isomers: X-Ray Crystal and Molecular Structure of 2β,14-Dibromo-4α,5β,6β,11βH-tetrahydrosantonin". . p. 495 - 496. Retrieved 1980.
• 2、 Blay, Gonzalo,Cardona, Luz,Garcia, Begona,Lahoz, Luisa,Pedro, Jose R.. "Synthesis of elemane bis-lactones from santonin - Synthesis of the reported structure of seco-isoerivanin pseudo acid and formal synthesis of (+)-8-deoxyvernolepin". . p. 2145 - 2151. Retrieved 2007/10/03.
• 3、 Shimizu,Akita,Oishi,Inayama. "A formal synthesis of l-α-santonin from chiral α,β-epoxyeudesmanolide via enzyme-catalyzed hydrolysis". . p. 1160 - 1162. Retrieved 2007/10/02.