1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine
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Basic information
- CAS
2226-96-2- Standard SMILES
CC1(C)CC(O)CC(C)(C)N1O- InChIKey
CSGAUKGQUCHWDP-UHFFFAOYSA-N- Molecular formula
- C9H19NO2
- Average molar mass
- 173.25 g/mol
- Monoisotopic mass
- 173.14157885
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
Properties
Computed structural propertiesFilling in
- XLogP
- 0.9
- Topological polar surface area
- 43.7 Ų
- 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
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
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
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
Acute Tox. 4 (100%)
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
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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
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.
Related reactions
144 records
Compound notes
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