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Santonin

CAS No.
481-06-1
Chemical Name:
Santonin
Synonyms
Semenen;SANTONIN;NSC 4900;A-SANTONIN;l-Santonin;α-santonin;Santonin>SANTONIN, A-;SANTONIN 97%;Santonin CRS
CBNumber:
CB2331234
Molecular Formula:
C15H18O3
Molecular Weight:
246.3
MDL Number:
MFCD00135865
MOL File:
481-06-1.mol
MSDS File:
SDS
Last updated:2024-04-15 08:55:32

Santonin Properties

Melting point 172-173 °C(lit.)
Boiling point 329.3°C (rough estimate)
Density 1.5900
refractive index -172.5 ° (C=2, CHCl3)
storage temp. 2-8°C
solubility Chloroform (Slightly)
color White to Off-White
Water Solubility 0.2g/L(17.5 ºC)
Merck 14,8361
BRN 89489
Stability Hygroscopic
LogP 1.600 (est)
CAS DataBase Reference 481-06-1(CAS DataBase Reference)
FDA UNII 1VL8J38ERO
EPA Substance Registry System Santonin (481-06-1)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301+H311+H331
Precautionary statements  P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
Hazard Codes  Xn,Xi,T+
Risk Statements  22-36/37/38-26/27/28
Safety Statements  22-24/25-45-37-36-28-26
RIDADR  2811
WGK Germany  3
RTECS  LE3150000
HS Code  2932.99.7000
HazardClass  6.1(a)
PackingGroup  II
NFPA 704
0
4 0

Santonin price More Price(28)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHL80931 α-Santonin phyproof?ReferenceSubstance 481-06-1 100mg $262 2024-03-01 Buy
Sigma-Aldrich S1250 (?)-α-Santonin ≥99% 481-06-1 5g $51.7 2022-05-15 Buy
Sigma-Aldrich 53653 (?)-α-Santonin analytical standard 481-06-1 10mg $118 2022-05-15 Buy
TCI Chemical S0521 Santonin >98.0%(HPLC)(T) 481-06-1 5g $80 2024-03-01 Buy
TCI Chemical S0521 Santonin >98.0%(HPLC)(T) 481-06-1 25g $316 2024-03-01 Buy
Product number Packaging Price Buy
PHL80931 100mg $262 Buy
S1250 5g $51.7 Buy
53653 10mg $118 Buy
S0521 5g $80 Buy
S0521 25g $316 Buy

Santonin Chemical Properties,Uses,Production

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.

History

The study on the chemical properties and structure of santonin was carried out at the end of the nineteenth century all the earliest research works were from the Italian scholars, such as Cannizzaro, Andreocci, Gucci, Francesconi, etc. The chemical structures determined before 1910 were all not exactly correct. Until 1929–1930, British scholars, Clemo, Haworth and Walton, finally determined the exact structure of santonin for the transformation from synthesized santonin into desmotroposanto nin and santonous acid. However, until 1940, there were no reports on structural configuration. Chinese scholars, Huang Minglong et al., basically completed the research work on the structural configuration of santonin in 1951, and the results were proved by Japanese scholars, Abe, Y. and Harukawa et al. in 1954.

Uses

(?)-α-Santonin has been used as a eudesmane-type sesquiterpene to study its effects on impairment of 231MFP breast cancer cell survival.

Uses

anthelmintic

Uses

(-)-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.

Definition

ChEBI: A santonin that is 3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione substituted by methyl groups at positions 3, 5a and 9.

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.

World Health Organization (WHO)

Santonin, a crystalline lactone obtained from flowerheads of species of Artemisia, was formerly used as an anthelminthic. Its use was associated with a range of adverse effects, mainly involving the sense organs and the central nervous system, some of which were fatal. It has been superseded by other less toxic and more effective anthelminthics.

General Description

(?)-α-Santonin is a sesquiterpene lactone. It is found in the genus Artemisia.

Biochem/physiol Actions

(?)-α-Santonin exhibits anti-helminthic properteis. It exhibits therapeutic effects against intestinal round worms.

Pharmacology

Santonin has a roundworm-expelling effect. It can excite worm’s ganglion which leads the worm not to be adsorbed in the intestinal wall, and then the worm is excreted out of the body after using laxatives. The effect is limited to the round worm, and it has little effect on other helminth. Excessive application can cause toxic effect. When it is excreted in urine, it can make the urine dark yellow or pink. It can be used in the treatment of ascariasis. During the medication, grease should be avoided, and laxative needs to be used such as salts. Patients with hepatosis, nephrosis and acute gastritis must contraindicate its use. The lethal dose 50 (LD50) injected under the skin of mice is 250–400 mg/kg.

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 on
Santonin 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.

18409-93-3
481-06-1
Synthesis of Santonin from 1,2-dihydro-alpha-santonin
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View Lastest Price from Santonin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Santonin 481-06-1 pictures 2022-02-14 Santonin 481-06-1
481-06-1
US $15.00 / g 1g ≥98% 1000.00 kgs NanJing Spring & Autumn Biological Engineering CO., LTD.
SANTONIN USP/EP/BP pictures 2021-06-19 SANTONIN USP/EP/BP
481-06-1
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
Santonin pictures 2020-04-28 Santonin
481-06-1
US $0.00-0.00 / Kg 1KG 99.0% 500 tons Shaanxi Dideu Medichem Co. Ltd
  • Santonin 481-06-1 pictures
  • Santonin 481-06-1
    481-06-1
  • US $15.00 / g
  • ≥98%
  • NanJing Spring & Autumn Biological Engineering CO., LTD.
  • Santonin pictures
  • Santonin
    481-06-1
  • US $0.00-0.00 / Kg
  • 99.0%
  • Shaanxi Dideu Medichem Co. Ltd
SANTONIN SANTONIN, A- (-)-Santonine [3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)dione 1,2,3,4,4a,7-Hexahydro-1-hydroxy-alpha, 4a,8-trimethyl-7-oxo-2-naphthaleneacetic acid gamma-lactone 11-Epiisoeusantona-1,4-dienic acid, 6alpha-hydroxy-3-oxo-, gamma-lactone 2-b)puran-2,8(3h,4h)-dione,3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-naphtho( 2-b]furan-2,8(3h,4h)-dione,3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-naphtho[ 3,5a,9-Trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione 3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnap-hthol[1,2-b]-furan-2,8(3H,4H)-dione 3aalpha,5abeta,9bbeta)]-[3s-(3alph (3S,3AS,5AS,9BS)-3,5A,9-TRIMETHYL-3A,5,5A,9B-TETRAHYDRO-3H,4H-NAPHTHO[1,2-B]FURAN-2,8-DIONE (3S,3AS,5AS,9BS)-3A,5,5A,9B-TETRAHYDRO-3,5A,9-TRIMETHYLNAPHTHO[1,2-B]FURAN-2,8(3H,4H)-DIONE (3S,5AS,9BS)-3A,5,5A,9B-TETRAHYDRO-3,5A,9-TRIMETHYLNAPHTHOL[1,2-B]FURAN-2,8(3H,4H)DIONE (-)-ALPHA-SANTONIN ALPHA-SANTONIN (3S,3aS,5aS,9bS)-2,3,3a,4,5,5a,8,9b-octahydro-3,5a,9-trimethylnaphtho(1,2-b)furan-2,8-dione SANTONIN 97% A-SANTONIN (3s,5as,9bs)-3a,5,5a,9b-tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3h,4h)dione SANTONIN, a-(RG) 1,2,3,4,4a,7-Hexahydro-1-hydroxy-a,4a,8-trimethyl-7-oxo-2-naphthaleneacetic acid g-lactone Eudesma-1,4-dien-12-oic acid, 6a-hydroxy-3-oxo-, g-lactone, (11S)- (8CI) Naphtho[1,2-b]furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)- (9CI) Naphtho[1,2-b]furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, [3S-(3a,3aa,5ab,9bb)]- NSC 4900 3,5a,9-trimethyl-2,3,3a,4,5,5a,8,9b-octahydronaphtho[1,2-b]furan-2,8-dione (3S)-3aβ,5,5a,9bα-Tetrahydro-3β,5aα,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione (3S)-3β,5aα,9-Trimethyl-3aβ,4,5,9bα-tetrahydronaphtho[1,2-b]furan-2,8(3H,5aH)-dione 4-dienicacid,6alpha-hydroxy-3-oxo-11-epiisoeusantona-gamma-lactone 6-alpha-hydroxy-3-oxo-,gamma-lactone,(11s)-(-eudesma-4-dien-12-oicacid 6-alpha-hydroxy-3-oxo-,gamma-lactone,(11s)-eudesma-4-dien-12-oicacid Eudesma-1,4-dien-12-oic acid, 6alpha-hydroxy-3-oxo-, gamma-lactone, (11S)- l-alpha-Santonin l-Santonin Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl- Naphtho[1,2-b]furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, [3S-(3alpha,3aalpha,5abeta,9bbeta)]- Santoninic anhydride santoninicanhydride Semenen 3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g]benzofuran-2,8-dione 3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g]benzofuran-2,8-quinone 3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-naphtho[7,8-d]furan-2,8-dione Eudesma-1,4-dien-12-oic acid, 6.alpha.-hydroxy-3-oxo-, .gamma.-lactone, (11R)- Naphtho(1,2-b)furan-2,8 Santonin 481-06-1 Santonin> Santonin CRS Naphtho[1,2-b]furan-2,8(3H,4H)-dione,3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)- (-)-Santonin SANTONIN USP/EP/BP α-santonin (3S,3aS,5aS,9bS)-3,5a,9-Trimethyl-3a,4,5,5a-tetrahydronaphtho[1,2-b]furan-2,8(3H,9bH)-dione (-)-alpha-santonin 2-Dihexadecanoyl-sn-glycero-3-phosphoethanolamine 2-Dimyristoyl-sn-glycero-3-PE 481-06-1 Furans