1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine (HCID 5395)

Überblick

hydroxylamine (protonated, reduced) form of TEMPOL; a N-hydroxyl form of LASTAR A; TEMPOL is paramagnetic radical used in NMR as SPIN LABELS whereas TEMPOL-H is not

Namen und Bezeichner

Bevorzugter Name: 1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine
IUPAC: 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol
Lokaler Name: 4-Hydroxy-2,2,6,6-tetramethylpiperidinoxyl
Englischer Name: 4-Hydroxy-TEMPO
Summenformel: C9H18NO2*
Molmasse: 172.24

Namen und Synonyme

3637-10-34-Piperidinol, 1-hydroxy-2,2,6,6-tetramethyl-TEMPOL-H1,4-dihydroxy-2,2,6,6-tetramethylpiperidineV55XB6IT82DTXSID408597114-hydroxy-2,2,6,6-tetramethyl-n-hydroxypiperidineOT 674N-Hydroxy-2,2,6,6-tetramethylpiperidine4-hydroxy-2,2,6,6-tetramethyl-1-hydroxypiperidine4-hydroxy-TEMPOLHOTMP

Weitere Namen anzeigen

4-OH-TEMPOTEMPOL4-Hydroxy-TEMPOZJ-701Inhibitor 701TMPN4-HO-TEMPO4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINYLOXY4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL

TEMPO-HRefChem:891347DTXCID80209756434-880-62,2,6,6-tetramethylpiperidine-1,4-diol1-hydroxy-2,2,6,6-tetramethyl-piperidin-4-ol1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol4-hydroxy tempo

Datenbank-Bezeichner

CAS: 2226-96-2、3637-10-3
PubChem CID: 5395
DTXSID: DTXSID40859711
ChEMBL: CHEMBL117649
UNII: V55XB6IT82
EC Number: 434-880-6、609-238-5
Nikkaji: J816.893H

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 0,9
Polarare Oberfläche (TPSA): 43,7 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 0
Schwere Atome: 12
Formalladung: 0
Komplexität: 159

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesBoiling point

Physikochemische Eigenschaften

Schmelzpunkt: 69 · 69-71 °C(lit.)
Siedepunkt: 302.58 °C · 302.58°C (rough estimate)
Dichte: 1.0402 · 1.0402 (rough estimate)
Dampfdruck: 0.025 Pa · 0.025Pa at 20℃
Brechungsindex: 1.435 · 1.4350 (estimate)
Flammpunkt: 146 ° · 146°(295°F)
storage temp.: 2 · 2-8°C
Löslichkeit: 1670 g/l · 1670g/l
Aggregatzustand: Crystals or Crystalline Powder
pka: 5.07 · 5.07[at 20 ℃]
Farbe: Orange
PH: 8.2 · 8.2 (20g/l, H2O, 20℃)
Wasserlöslichkeit: soluble
Merck: 14 · 14,9141
BRN: 1422990 · 1422990
Henry's Law Constant: 3.3 · 3.3×109 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität: Stable. Incompatible with strong oxidizing agents.
Kosmetik-Inhaltsstoffe Funktionen: ANTIOXIDANT
InChI: 1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3
InChIKey: FAPCFNWEPHTUQK-UHFFFAOYSA-N
SMILES: CC1(C)CC(O)CC(C)(C)N1[O]
LogP: 0.56 at · 0.56 at 25℃
CAS Datenbank: 2226 · 2226-96-2(CAS DataBase Reference)
NIST chemische Informationen: 1 · 1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl-(2226-96-2)
EPA chemische Informationen: 1 · 1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl- (2226-96-2)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P319, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Gefahrenhinweise

Regulatory Information · 2 Einträge

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 25-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/16531

Hazard Classes and Categories · 2 Einträge

Acute Tox. 4 (100%)

Sicherheitsdaten

wgk: 1
tsca: TSCA listed
hs_code: 29333999
RTECS-Nr.: TN8991000
risk_code: 22-36/37/38-36/38
Toxizität: LD50 oral in rat: 1053mg/kg
hazard_code: Xn,Xi
safety_code: 26-36-37/39-36/37/39-27
Speicherklasse: 11 - Combustible Solids
Giftige Stoffe Daten: 2226-96-2(Hazardous Substances Data)
Hazard Classifications: Acute Tox. 4 OralEye Dam. 1STOT RE 2 Oral
Selbstentzündungstemperatur: 260°C (DIN 51794)

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.

Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military.

Verwendung und Herstellung

General Manufacturing Information4-Piperidinol, 1-hydroxy-2,2,6,6-tetramethyl-: ACTIVE

Anwendungen · 2 Einträge

BeschreibungTEMPOL is a piperidine nitroxide and spin label with superoxide dismutase (SOD) mimetic activity. It inhibits lipid peroxidation in rat liver microsomes with 50% inhibition of microsomal lipid peroxidation (IP50) values of 117, 61, and 381 μM for peroxidation induced by iron plus NADPH, iron plus ascorbate, and t-butylhydroperoxide, respectively. TEMPOL (1 mM) inhibits production of superoxide anions by 92% via a xanthine-xanthine oxidase reaction in vitro. It reduces mean arterial pressure and heart rate in spontaneously hypertensive rats (ED50s = 70 and 63 μmol/kg, respectively) when administered intravenously. TEMPOL is a cell-permeable spin label that has been used to quantify intracellular oxygen in various cell types by electron spin resonance (ESR) spectroscopy.

VerwendenA free radical scavenger