Kirenol
Basic information
- CAS
52659-56-0- Standard SMILES
C[C@@]1(CO)C[C@@H](O)C[C@@]2(C)[C@@H]3CC[C@](C)([C@@H](O)CO)C=C3CC[C@H]12- InChIKey
NRYNTARIOIRWAB-JPDRSCFKSA-N- Molecular formula
- C20H34O4
- Average molar mass
- 338.5 g/mol
- Monoisotopic mass
- 338.24570956
Overview
Kirenol is a diterpenoid.
Names & identifiers
- Preferred name
- Kirenol
- IUPAC
- (1R)-1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol
- English name
- KIRENOL
- Molecular formula
- C20H34O4
- Molecular weight
- 338.49
Names & synonyms
Kirenol52659-56-0(1R)-1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol(1R)-1-((2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl)ethane-1,2-diolRefChem:151275Kirenol (Standard)MFCD00210519(R)-1-((2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-2-yl)ethane-1,2-diolKirenol 100 |Ig/mL in AcetonitrileKirenol 100 microg/mL in Acetonitrileorb1302297orb3140451
Show more names
KirelKIRENOL(P)Kirenol, 10 mM in DMSO(1R,3S,4aS,4bS,7S,10aS)-1,2,3,4,4a,4b,5,6,7,9,10,10a-Dodecahydro-3-hydroxy-7-[(R)-1,2-dihydroxyethyl]-1,4a,7-trimethylphenanthrene-1-methanol1,7-Phenanthrenedimethanol, 1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-3-hydroxy-α7-(hydroxymethyl)-1,4a,7-trimethyl-, (α7R,1R,3S,4aS,4bR,7S,10aS)-1,7-PhenanthrenediMethanol,1,2,3,4,4a,4b,5,6,7,- 9,10,10a-dodecahydro-3-hydroxy-R7- (hydroxyMethyl)-1,4a,7-triMethyl-,(R7R,1R,- 3S,4aS,4bR,7S,10aS)-
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 80.9 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 518
Physicochemical properties
- Melting point
- 197 to · 197.0 to 201.0 °C
- Boiling point
- 516.9 · 516.9±35.0 °C(Predicted)
- Density
- 1.17 · 1.17±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Ethanol (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 14.06 · 14.06±0.20(Predicted)
- color
- White to Light Yellow
- Major Application
- food and beverages
- Cosmetics Ingredients Functions
- ANTIMICROBIALHAIR CONDITIONINGSKIN CONDITIONING - EMOLLIENTANTIOXIDANT
- InChI
- InChI=1/C20H34O4/c1-18(17(24)11-21)7-6-15-13(8-18)4-5-16-19(2,12-22)9-14(23)10-20(15,16)3/h8,14-17,21-24H,4-7,9-12H2,1-3H3/t14-,15-,16-,17+,18+,19+,20+/s3
- InChIKey
- NRYNTARIOIRWAB-QNOIMPALNA-N
- SMILES
- C[C@@]12C[C@H](O)C[C@@](C)(CO)[C@@]1([H])CCC1=C[C@@](C)([C@@H](O)CO)CC[C@@]21[H] |&1:1,3,6,10,16,18,24,r|
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- rtecs
- SF7352310
- hs_code
- 29399990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionKirenol is a diterpenoid that has been found in S. orientalis and has diverse biological activities, including anti-arthritic and anti-inflammatory properties. It inhibits Gram-positive and Gram-negative bacterial growth in disc diffusion assays with MICs ranging from 39 to 156 and 312.5 to 625 μg/ml, respectively. Kirenol also reduces K652 chronic myeloid leukemia cell viability with a 48 hour IC50 value of 18.19 μg/ml and induces apoptosis. In vivo, kirenol (2 mg/kg, p.o.) reduces motor deficit, delays disease onset by approximately five days, and downregulates inflammatory CD4+IFN-γ+ Th1 cells and CD4+IL-17A+ Th17 cells in a mouse model of experimental autoimmune encephalomyelitis (EAE). Intragastric administration of kirenol (1-4 mg/kg) reduces the arthritis index, NF-kB activity, and paw swelling and increases annexin-1 expression without affecting glucocorticoid receptor α (GRα) expression in the synovium in a rat model of collagen-induced arthritis. Topical administration of kirenol (0.3-0.5% w/w) reduces edema induced by carrageenan, complete Freund''s adjuvant (CFA), and formalin in rats up to 44, 67, and 65%, respectively.
UsesKirenol is a pharmaceutical agent that induces apoptosis in human chronic myeloid leukemia cells.
Additional notes
DefinitionChEBI: Kirenol is a diterpenoid.
Related reactions
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Compound notes
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