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

Overview

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

Names & identifiers

Preferred name: 1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine
IUPAC: 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol
English name: 4-Hydroxy-TEMPO
Molecular formula: C9H18NO2*
Molecular weight: 172.24

Names & synonyms

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

Show more names

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

Database identifiers

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

Properties

Computed structural properties

XLogP: 0.9
Topological polar surface area: 43.7 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 0
Heavy atoms: 12
Formal charge: 0
Complexity: 159

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesBoiling point

Physicochemical properties

Melting point: 69 · 69-71 °C(lit.)
Boiling point: 302.58 °C · 302.58°C (rough estimate)
Density: 1.0402 · 1.0402 (rough estimate)
vapor pressure: 0.025 Pa · 0.025Pa at 20℃
refractive index: 1.435 · 1.4350 (estimate)
Flash point: 146 ° · 146°(295°F)
storage temp.: 2 · 2-8°C
solubility: 1670 g/l · 1670g/l
form: Crystals or Crystalline Powder
pka: 5.07 · 5.07[at 20 ℃]
color: Orange
PH: 8.2 · 8.2 (20g/l, H2O, 20℃)
Water Solubility: soluble
Merck: 14 · 14,9141
BRN: 1422990 · 1422990
Henry's Law Constant: 3.3 · 3.3×109 mol/(m3Pa) at 25℃, HSDB (2015)
Stability: Stable. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions: 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 DataBase Reference: 2226 · 2226-96-2(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 78 ZX2F65X · U78ZX2F65X
NCI Drug Dictionary: Tempol
NIST Chemistry Reference: 1 · 1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl-(2226-96-2)
EPA Substance Registry System: 1 · 1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl- (2226-96-2)
UNSPSC Code: 12352200 · 12352200
NACRES: 77 · NA.77
Symbol(GHS): 5 · GHS05,GHS07
Signal word: Danger
Hazard statements: 302 · H302-H318
Precautionary statements: 264 · P264-P270-P280-P301+P312-P305+P351+P338-P501
target organs: Liver,spleen
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn,Xi
Risk Statements: 22 · 22-36/37/38-36/38
Safety Statements: 26 · 26-36-37/39-36/37/39-27
WGK Germany: 1 · 1
RTECS: 8991000 · TN8991000
Autoignition Temperature: 260 °C · 260°C (DIN 51794)
TSCA: TSCA listed
HS Code: 29333999 · 29333999
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Dam. 1STOT RE 2 Oral
Hazardous Substances Data: 2226 · 2226-96-2(Hazardous Substances Data)
Toxicity: 50 oral · LD50 oral in rat: 1053mg/kg
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 6 items

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]

Hazard information

Regulatory Information · 2 items

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 items

Acute Tox. 4 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 1
tsca: TSCA listed
rtecs: TN8991000
hs_code: 29333999
Toxicity: LD50 oral in rat: 1053mg/kg
risk_code: 22-36/37/38-36/38
Signal word: Danger
Symbol(GHS): GHS05,GHS07
hazard_code: Xn,Xi
safety_code: 26-36-37/39-36/37/39-27
Storage Class: 11 - Combustible Solids
target organs: Liver,spleen
Hazard statements: H302-H318
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralEye Dam. 1STOT RE 2 Oral
Autoignition Temperature: 260°C (DIN 51794)
Precautionary statements: P264-P270-P280-P301+P312-P305+P351+P338-P501
Hazardous Substances Data: 2226-96-2(Hazardous Substances Data)

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

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.

Uses & manufacturing

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

Applications · 5 items

DescriptionTEMPOL 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.

UsesA free radical scavenger

UsesSpin label for EPR studies; phase transfer dehydration catalyst; antioxidant; inhibitor of olefin free radical polymerization.

UsesTempol, a water-soluble piperidine nitroxide derivative having nonspecific radical-scavenging and superoxide dismutase (SOD) activity, protects cultured aerobic, but not hypoxic, cells against radiation-induced killing. Protection does not depend on intracellular thiols and does not involve O2-depletion. Tempol reacts with peroxyl radicals and can also oxidize DNA-bound metal ions, thereby interfering with OH generation.

General Description4-Hydroxy-TEMPO is a 4-substituted 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) derivative. It is a low-molecular weight compound and has been proposed as superoxide dismutase mimic.