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Toosendanin

HCID 9851101
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
58812-37-6
Standard SMILES
CC(=O)O[C@@H]1C[C@H](O)[C@@]23CO[C@@H](O)[C@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@@H]3C(=O)[C@H](OC(C)=O)[C@@]2(C)[C@H](c3ccoc3)C[C@H]3O[C@]321
InChIKey
NAHTXVIXCMUDLF-RFNFAWMESA-N
Molecular formula
C30H38O11
Average molar mass
574.6 g/mol
Monoisotopic mass
574.24141202

Overview

Toosendanin is a limonoid.

Names & identifiers

Preferred name
Toosendanin
IUPAC
[(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16R,19S,21R)-4-acetyloxy-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate
English name
Toosendanin
Molecular formula
C30H38O11
Molecular weight
574.62

Names & synonyms

Toosendanin58812-37-6[(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16R,19S,21R)-4-Acetyloxy-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate((1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16R,19S,21R)-4-acetyloxy-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo(13.3.3.01,14.02,11.05,10.08,10)henicosan-21-yl) acetateRefChem:898613ChuanliansuMFCD00210564C30H38O1112-AcetoxyamoorastatinCHEBI:192461AKOS025311566(1S,2aR,3aS,3bS,4R,5aR,6R,7R,9S,9aS,9bR,11R,11aR,14R)-1-(Furan-3-yl)-4,9,14-trihydroxy-3b,6,11a-trimethyl-10-oxotetradecahydro-1H-6,9a-(methanooxymethano)naphtho[1',2':6,7]indeno[1,7a-b]oxirene-7,11-diyl diacetate
Show more names
ToosendaniToosendaninrToosendan extractToosendan Fructus。28-DeacetylsendaninToosendanin USP/EP/BPToosendanin 58812-37-6
CHEMBL503044orb1300256HY-N0263EBC-617126FT65803T6S0234AS-56295CS-0008285

Database identifiers

CAS
58812-37-6
PubChem CID
9851101
DTXSID
DTXSID00974333
ChEMBL
CHEMBL503044
ChEBI
CHEBI:192461
EC Number
683-199-2
Nikkaji
J612.432A

Properties

Computed structural properties

XLogP
0.7
Topological polar surface area
165 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
11
Rotatable bonds
5
Heavy atoms
41
Formal charge
0
Complexity
1,190

Physicochemical properties

Melting point
170 · 170-175°C
Boiling point
555.97 °C · 555.97°C (rough estimate)
Density
1.2084 · 1.2084 (rough estimate)
refractive index
1.597 · 1.5970 (estimate)
storage temp.
Refrigerator
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid
pka
12.15 · 12.15±0.70(Predicted)
color
White to Pale Beige
InChIKey
NAHTXVIXCMUDLF-VJLDGHPTNA-N
SMILES
C[C@@]1([C@H]2OC(C)=O)[C@]3([C@]([H])(O3)C[C@H]1C4=COC=C4)[C@]5(C)[C@H](O)C[C@@]6([H])[C@@](C)([C@@H]7O)[C@H](OC(C)=O)C[C@H](O)[C@]6(CO7)[C@@]5([H])C2=O
CAS DataBase Reference
58812 · 58812-37-6
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301
Precautionary statements
264 · P264-P270-P301+P310-P321-P330-P405-P501
Safety Statements
24 · 24/25
WGK Germany
3 · WGK 3
HS Code
29389090 · 29389090
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 Oral · Acute Tox. 3 Oral

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

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety data

wgk
WGK 3
hs_code
29389090
Signal word
Danger
Symbol(GHS)
GHS06
safety_code
24/25
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard statements
H301
Hazard Classifications
Acute Tox. 3 Oral
Precautionary statements
P264-P270-P301+P310-P321-P330-P405-P501

Chemistry & industry

Applications · 4 items

DescriptionFructus Meliae Toosendan (chuan lian zi), the fruit of Melia toosendan Sieb. Et Zucc, is mainly produced in Sichuan, Hubei, Henan, and Hunan province in China . Toosendanin is a tetracyclic triterpene compound extracted from fructus toosendan. It is an ascaridole agent and showed anti-botulinum, antibacterial, anticancer, and anti-inflammatory effects. It is also a neuromuscular blocking agent.

HistoryToosendanin is the main chemical composition of the fructus toosendan. Researches on this compound could date back to 1953. Toosendanin has been named in 1955, while its structure was identified 20 years later by mass spectrometry. Toosendanin is a triterpenoid derivative containing a β-substituted furan ring . A new synthetic strategy is put forth allowing access to a 4-acetoxy CD fragment analogue of toosendanin, which was achieved from mesityl oxide and acetylacetone in 14 steps in 2009 . The anti-parasite of toosendanin was reported in 1971. In 1980, it was identified as a selective neuromuscular blocking agent that acts on neuromuscular junction . The anti-botulinum effect of toosendanin was discovered in 1982 . In recent years, it is also observed that toosendanin can induce differentiation and apoptosis . Toosendanin could inhibit the growth of feeding larvae and insects. It has been used as pollution-free, no residue of botanical insecticides for the production of fruits and vegetables in China .

UsesToosendanin is a triterpenoid derivative, acts as a novel agonist of L-type Ca2+ channels in neonatal rat ventricular cells.

UsesToosendanin is a triterpenoid derivative and a novel agonist of L-type Ca2+ channels in neonatal rat ventricular cells (1,2,3).

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
西安泽邦生物科技有限公司[email protected]
天津万象恒远科技有限公司15722085254 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
上海融禾医药科技发展有限公司17301719108 13341702378 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
深圳虹彩祥根生物科技有限公司+86-0755-89668383 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
杭州东帆化学有限公司86-0571-85151182
Aktin Chemicals, Inc.028-85159085 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
成都瑞芬思德丹生物科技有限公司2355253622; 18981954830 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
Labnetwork lnc.+86-27-50766799 +86-18062016861 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
湖北康恩化学有限公司180-64105258 18064105258 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Wuhan ChemNorm Biotech Co.,Ltd.+86-27-8439 4403 18971486879 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
郑州阿尔法化工有限公司0371-53765687 18937137882 · [email protected]
上海岚克医药科技发展有限公司0086-21-58956006
南京择优新材料科技有限公司173-40521416 17340521416 · [email protected]
上海西陇生化科技有限公司021-52907766-8042

Additional notes

DefinitionChEBI: Toosendanin is a limonoid.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes