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alpha-Santonin

HCID 221071
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Grundinformationen

CAS
481-06-1
Standard-SMILES
CC1=C2[C@H]3OC(=O)[C@@H](C)[C@@H]3CC[C@@]2(C)C=CC1=O
InChIKey
XJHDMGJURBVLLE-BOCCBSBMSA-N
Summenformel
C15H18O3
Durchschnittliche Molmasse
246,306 g/mol
Monoisotopische Masse
246,12559444

Namen und Bezeichner

Bevorzugter Name
alpha-Santonin
IUPAC
(3S,3aS,5aS,9bS)-3,5a,9-Trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione
Lokaler Name
alpha-Santonin
Englischer Name
Santonin
Summenformel
C15H18O3
Molmasse
246.3

Namen und Synonyme

α-santoninALPHA-SANTONIN(-)-Santonin(-)-Santonine(?)-α-SantoninSemenenSANTONINNSC 4900A-SANTONINl-Santonin

Datenbank-Bezeichner

CAS
481-06-1
PubChem CID
221071
DTXSID
DTXSID7045312
ChEMBL
CHEMBL259254
ChEBI
CHEBI:16363
UNII
1VL8J38ERO
EC Number
207-560-7
Nikkaji
J6.172G

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt
172 · 172-173 °C(lit.)
Siedepunkt
329.3 °C · 329.3°C (rough estimate)
Dichte
1.59 · 1.5900
Brechungsindex
-172.5 ° · -172.5 ° (C=2, CHCl3)
storage temp.
2 · 2-8°C
Löslichkeit
Chloroform (Slightly)
Aggregatzustand
Solid
Farbe
White to Off-White
Wasserlöslichkeit
0.2 g/L · 0.2g/L(17.5 ºC)
Merck
14 · 14,8361
BRN
89489 · 89489
Stabilität
Hygroscopic
InChI
1S/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
InChIKey
XJHDMGJURBVLLE-BOCCBSBMSA-N
SMILES
C[C@H]1[C@@H]2CC[C@@]3(C)C=CC(=O)C(C)=C3[C@H]2OC1=O
LogP
1.6 · 1.600 (est)
CAS Datenbank
481 · 481-06-1(CAS DataBase Reference)
EPA chemische Informationen
Santonin (481-06-1)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
2811
hs_code
2932.99.7000
RTECS-Nr.
LE3150000
risk_code
22-36/37/38-26/27/28
hazard_code
Xn,Xi,T+
safety_code
22-24/25-45-37-36-28-26
hazard_class
6.1(a)
packing_group
II
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral

Chemie und Industrie

Anwendungen · 3 Einträge

BeschreibungSantonin 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.

HistoryThe 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.

Verwenden(-)-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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

HydrogenchloridCalciumdihydroxid

Nachgelagerte Produkte

(1S,αS)-1,2,3,4,4a,7-Hexahydro-1β-hydroxy-α,4aα,8-trimethyl-7-oxonaphthalene-2α-acetic acid(3S)-8-Hydroxyimino-3aβ,4,5,5a,8,9bα-hexahydro-3β,5aα,9-trimethylnaphtho[1,2-b]furan-2(3H)-one(3R)-3aβ,5,5a,9bβ-Tetrahydro-3α,5aα,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione

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Ergänzende Hinweise

DefinitionChEBI: 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.

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