Resiniferatoxin (HCID 5702546)

Überblick

Resiniferatoxin is a heteropentacyclic compound found in Euphorbia poissonii with molecular formula C37H40O9. It is an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1). It has a role as a TRPV1 agonist, an analgesic, a neurotoxin and a plant metabolite. It is a tertiary alpha-hydroxy ketone, a diterpenoid, a monomethoxybenzene, a carboxylic ester, a member of phenols, an organic heteropentacyclic compound, an enone and an ortho ester.

Namen und Bezeichner

Bevorzugter Name: Resiniferatoxin
IUPAC: [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
Englischer Name: RESINIFERATOXIN
Summenformel: C37H40O9
Molmasse: 628.71

Namen und Synonyme

Resiniferatoxin57444-62-9ReciniferatoxinLopain(+)-resiniferatoxinRTX diterpeneMtx-071NeuroclastinA5O6P1UL4IMTX-71DTXSID00894764CHEBI:8809

Weitere Namen anzeigen

RTX[3H]resiniferatoxinResiniferatoxin >99%Resiniferatoxin (80%)Resiniferatoxin, 98.5%RESINIFERATOXIN,HIGHPURITYDSDNAKHZNJAGHN-IHCAYWNCSA-NRESINIFERATOXIN, 99%, HIGH PURITYRESINIFERATOXIN,EUPHORBIA POISONII

[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate6,7-Deepoxy-6,7-didehydro-5-deoxy-21-dephenyl-21-(phenylmethyl)daphnetoxin 20-(3-hydroxy-5-methoxybenzeneacetate)Benzeneacetic acid, 4-hydroxy-3-methoxy-, ((2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methylethenyl)-7-oxo-2-(phenylmethyl)-7H-2,9b-epoxyazuleno(5,4-e)-1,3-benzodioxol-5-yl)methyl ester((1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo(11.4.1.01,10.02,6.011,15)octadeca-3,8-dien-8-yl)methyl 2-(4-hydroxy-3-methoxyphenyl)acetateRefChem:879415DTXCID501324327((1R,2R,6R,10S,11R,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo(11.4.1.01,10.02,6.011,15)octadeca-3,8-dien-8-yl)methyl 2-(4-hydroxy-3-methoxyphenyl)acetate((1R,2R,6R,10S,11R,15S,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo(11.4.1.01,10.02,6.011,15)octadeca-3,8-dien-8-yl)methyl 2-(4-hydroxy-3-methoxyphenyl)acetate

Datenbank-Bezeichner

CAS: 57444-62-9
PubChem CID: 5702546
DTXSID: DTXSID00894764
ChEMBL: CHEMBL17976
ChEBI: CHEBI:8809
UNII: A5O6P1UL4I
EC Number: 637-354-6
Nikkaji: J282.917G

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 4,5
Polarare Oberfläche (TPSA): 121 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 9
Frei drehbare Bindungen: 9
Schwere Atome: 46
Formalladung: 0
Komplexität: 1.330

Physikochemische Eigenschaften

Siedepunkt: 768.7 · 768.7±60.0 °C(Predicted)
Dichte: 1.35 · 1.35±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
Löslichkeit: 100 mM · Soluble in DMSO to 100mM and to 50mM in ethanol
Aggregatzustand: Solid
pka: 9.85 · 9.85±0.20(Predicted)
Farbe: White to off-white
Biologische Quelle: Euphorbia poisonii
BRN: 5371150 · 5371150
Stabilität: 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey: DSDNAKHZNJAGHN-MXTYGGKSSA-N
SMILES: C1(CC(OCC2C[C@@]3(O)[C@]([H])([C@]45O[C@]6(CC7=CC=CC=C7)O[C@]([H])([C@]4([H])C=2)[C@](C(C)=C)(C[C@H]5C)O6)C=C(C)C3=O)=O)=CC=C(O)C(OC)=C1

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

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

P260, P264, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxikologische Informationen

Health EffectsResiniferatoxin is a neurotoxin that targets afferent sensory neurons involved in nociception. It evokes a powerful irritant effect followed by desensitization and analgesia. (L1244)

Exposure RoutesOral (ingestion) (L1817) ; dermal (L1817)

Toxicity Summary · 1 Eintrag

Resiniferatoxin activates the vanilloid receptor in a subpopulation of primary afferent sensory neurons involved in nociception (the transmission of physiological pain). RTX causes a novel ion channel in the plasma membrane of sensory neurons, the transient receptor potential vanilloid 1, to become permeable to cations, most particularly the calcium cation. This evokes a powerful irritant effect followed by desensitization and analgesia. (L1244)

Signs and SymptomsResiniferatoxin evokes a powerful irritant effect followed by desensitization and analgesia. (L1244)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

F: 10-23
wgk: 3
ridadr: UN 2928 6.1/PG 2
hs_code: 29329990
RTECS-Nr.: CY1633700
risk_code: 25-35
hazard_code: T
safety_code: 26-36/37/39-45
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 OralSkin Corr. 1A

Chemie und Industrie

Verwendung und Herstellung

Uses · 1 Eintrag

Resiniferatoxin (RTX) is a plant toxin and ultrapotent capsaicin analog that occurs in various species of plants, such as resin spurge (Euphorbia resinifera). (L1244) Investigated for use/treatment in interstitial cystitis and urinary incontinence.

Anwendungen · 1 Eintrag

VerwendenResiniferatoxin has been used as an agonist to transient receptor potential vanilloid 2 (TRPV2): for complex preparation for cryo-electron microscopy structural studies to test its effect towards immune responses toP.aeruginosa in sensory neurons associated with the cornea to study its effects in the denervation of the peripheral sensory nerves in psoriatic mice

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Benzeneacetic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxy-4-Hydroxy-3-methoxyphenylessigsure

Anbieter50 Anbieter

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]

成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]

陕西缔都新材料有限公司81124267 17392282731 · [email protected]

上海哲研生物科技有限公司021-18017610038 18017610038 · [email protected]

成都健腾生物技术有限公司028-85159085 · [email protected]

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