481-06-1 Usage
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
Different sources of media describe the Uses of 481-06-1 differently. You can refer to the following data:
1. anthelmintic
2. (-)-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.
3. (?)-α-Santonin has been used as a eudesmane-type sesquiterpene to study its effects on impairment of 231MFP breast cancer cell survival.
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 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.
Check Digit Verification of cas no
The CAS Registry Mumber 481-06-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 1 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 481-06:
(5*4)+(4*8)+(3*1)+(2*0)+(1*6)=61
61 % 10 = 1
So 481-06-1 is a valid CAS Registry Number.
InChI:InChI=1/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13+,15+/m0/s1
481-06-1Relevant articles and documents
-
Borsutzki
, p. 336,337 (1955)
-
Synthetic approach to exo-endo cross-conjugated cyclohexadienones and its application to the syntheses of dehydrobrachylaenolide, isodehydrochamaecynone, and trans-isodehydrochamaecynone
Higuchi, Yohsuke,Shimoma, Fumito,Koyanagi, Rei,Suda, Kouji,Mitsui, Tomokazu,Kataoka, Takao,Nagai, Kazuo,Ando, Masayoshi
, p. 588 - 594 (2007/10/03)
Methodology for synthesis of exo-endo cross-conjugated dienones with trans- and cis-decalin systems has been reported. Bromination of the silyl enol ether of α′-methyl α,β-unsaturated ketones with PTAB and successive dehydrobromination of the resulting α′-bromo-α′-methyl α,β-unsaturated ketones under three conditions (DBU/PhH; TBAF/THF; Li2CO3, LiBr/DMF) gave the desired exo-endo cross-conjugated dienones in good yield. This method was applied to the syntheses of dehydrobrachylaenolide (1), isodehydro-chamaecynone (5c), and trans-isodehydrochamaecynone (11) starting from tuberiferine (7), chamaecynone (5a), and trans-chamaecynone (9). Eudesmanolides possessing an α-methylene γ-lactone moiety, i.e., 1, 7, and 13, exhibited significant inhibitory activity toward the induction of the intercellular adhesion molecule-1 (ICAM-1). Compound 1 showed greater activity than 7 and 13. All compounds possessing an ethynyl group, 5d, 9, 11, and 14, showed the same degree of termiticidal activity, and the exo-endo cross-conjugated dienone structure in 11 had no influence on the activity.
A short-step synthesis of sesquiterpene lactone, 1-oxoeudesma-2,4-dien-11βh-12, 6α-olide, isolated from artemisia herba-alba and its derivatives
Kawamata,Nagashima,Nakai,Tsuji
, p. 139 - 148 (2007/10/03)
1-Oxoeudesma-2,4-dien-11βH-12,6α-olide(1) isolated from the genus Artemisia herb-alba was synthesized from α-santonin in a two-step sequence. The key step is the 1,3 oxidative rearrangement of dienol 7.
Synthetic Transformation of Santonin into (5α,7α,11β)-3,6-Dioxogermacr-1-en-13,7-olide, a New Intermediate for Germacranes and Guaianes
Harapanhalli, Ravi S.
, p. 1009 - 1012 (2007/10/02)
A seven-step synthesis of a new intermediate (5α,7α,11β)-3,6-dioxogermacr-1-en-13,7-olide (10) is described starting from (-)-α-santonin (1).The key step in the transformation was photolytic skeletal rearrangement of (4α,5β,6α,11β)-5-hydroxy-2-oxoeudesman-13,6-olide (9) to the title compound, sensitised by mercuric oxide and iodine.
