HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

(-)-Santonin

HCID 221071
New noteNew reactionRequest quotes
Print preview
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

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
Molecular formula
C15H18O3
Average molar mass
246.3 g/mol
Monoisotopic mass
246.12559443

Overview

Alpha-santonin is 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. It has a role as a plant metabolite. It is a santonin and a botanical anti-fungal agent.

Names & identifiers

Preferred name
(-)-Santonin
IUPAC
(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
English name
Santonin
Molecular formula
C15H18O3
Molecular weight
246.3

Names & synonyms

santoninalpha-Santonin481-06-1Semenen(-)-SantoninSantoninumSantoninic anhydrideL-alpha-SantoninDTXSID7045312NSC-49001VL8J38ERO(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione
Show more names
α-santonin(-)-Santonine(?)-α-SantoninNSC 4900A-SANTONINl-Santonin
(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dioneDTXCID5025312CHEBI:16363(3S,3AS,5AS)-3,5A,9-TRIMETHYL-3A,4,5,5A-TETRAHYDRONAPHTHO(1,2-B)FURAN-2,8(3H,9BH)-DIONE(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo(g)(1)benzofuran-2,8-dione(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho(1,2-b)furan-2,8(3H,4H)-dioneRefChem:56700Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S-(3alpha,3aalpha,5abeta,9bbeta))-

Database identifiers

CAS
481-06-1
PubChem CID
221071

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
43.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
18
Formal charge
0
Complexity
500

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]
Collision Cross Section · 2 items

154.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

154.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
172 · 172-173 °C(lit.)
Boiling point
329.3 °C · 329.3°C (rough estimate)
Density
1.59 · 1.5900
refractive index
-172.5 ° · -172.5 ° (C=2, CHCl3)
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly)
form
Solid
color
White to Off-White
Water Solubility
0.2 g/L · 0.2g/L(17.5 ºC)
Merck
14 · 14,8361

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H302 (98.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (98.6%)

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
LE3150000
ridadr
2811
hs_code
2932.99.7000
risk_code
22-36/37/38-26/27/28
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
Xn,Xi,T+
safety_code
22-24/25-45-37-36-28-26
hazard_class
6.1(a)
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
II

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances used in the treatment or control of nematode infestations. They are used also in veterinary practice.

Uses & manufacturing

General Manufacturing InformationNaphtho[1,2-b]furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-: INACTIVE
Applications · 6 items

DescriptionSantonin 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.

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes
DTXSID
DTXSID7045312
ChEMBL
CHEMBL259254
ChEBI
CHEBI:16363
UNII
1VL8J38ERO
EC Number
207-560-7
Nikkaji
J6.172G
BRN
89489 · 89489
Stability
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 DataBase Reference
481 · 481-06-1(CAS DataBase Reference)
FDA UNII
1 VL8J38ERO · 1VL8J38ERO
EPA Substance Registry System
Santonin (481-06-1)
UNSPSC Code
41116107 · 41116107
NACRES
83 · NA.83
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301+H311+H331
Precautionary statements
280 · P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
PPE
3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
Xn,Xi,T+
Risk Statements
22 · 22-36/37/38-26/27/28
Safety Statements
22 · 22-24/25-45-37-36-28-26
RIDADR
2811 · 2811
WGK Germany
3 · 3
RTECS
3150000 · LE3150000
TSCA
TSCA listed
HS Code
2932.99 · 2932.99.7000
HazardClass
6.1 · 6.1(a)
PackingGroup
II
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
Hazard statements
H301+H311+H331
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
Precautionary statements
P280-P301+P310+P330-P302+P352+P312-P304+P340+P311

Usesanthelmintic

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

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.

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

Upstream & downstream products

Upstream raw materials

Hydrochloric acidCalcium hydroxide

Downstream products

(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

Additional notes

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.