Basic information
- CAS
489-32-7- Standard SMILES
COc1ccc(-c2oc3c(CC=C(C)C)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)ccc3c(=O)c2OC[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)cc1- InChIKey
HFQPKOQLZSCHPI-HATIIQGLSA-N- Molecular formula
- C34H42O14
- Average molar mass
- 674.7 g/mol
- Monoisotopic mass
- 674.25745601
Names & identifiers
- Preferred name
- 4H-1-Benzopyran-4-one, 3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-
- IUPAC
- 2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxy]chromen-4-one
- English name
- Icariin
- Molecular formula
- C33H40O15
- Molecular weight
- 676.66
Names & synonyms
SCHEMBL3126142-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]methoxy]chromen-4-one4H-1-Benzopyran-4-one, 3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-epimedium extractHorny goat weed extractICARINICARRINICARIINEIcraiinEpimedium Extract Icariin4H-1-Benzopyran-4-one, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-7-(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[[(2S,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-3-[[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-2-oxanyl]oxy]-1-benzopyran-4-one
Show more names
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Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 214 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 10
- Heavy atoms
- 48
- Formal charge
- 0
- Complexity
- 1,150
Physicochemical properties
- Melting point
- 223 · 223-225 ºC
- alpha
- 15 · D15 -87.09° (in pyridine)
- Boiling point
- 948.5 · 948.5±65.0 °C(Predicted)
- Density
- 1.55 · 1.55
- RTECS
- 2980500 · DJ2980500
- storage temp.
- 2 · 2-8°C
- solubility
- 50 mg/mL, · DMSO: soluble50mg/mL, clear, colorless to dark yellow
- form
- Powder
- pka
- 5.9 · 5.90±0.40(Predicted)
- color
- light yellow to yellow
- λmax
- 350 nm · 350nm(MeOH)(lit.)
- Merck
- 14 · 14,3617
- Stability
- Light Sensitive
- InChIKey
- TZJALUIVHRYQQB-XLRXWWTNSA-N
- SMILES
- COc1ccc(cc1)C2=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C(=O)c4c(O)cc(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)c(C\C=C(\C)C)c4O2
- LogP
- 1.736 · 1.736 (est)
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
- 3
- hs_code
- 29389090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Applications
DescriptionIcariin is one of the major flavonoids of the herb Epimedium, which has long been used in Tranditional Chinese Medicine to treat bone fracture and prevent osteoporosis. Research has shown that icariin should be an effective component for the bone-strengthening activity of the herb Epimedium, and one of the possible mechanisms for this activity is to stimulate the proliferation and enhance the osteogenic differentiation of marrow stromal cells. Icariin is reported to prevent and treat sexual dysfunction related diseases and improve the use of vasoconstriction. Icariin is used to prepare angiotensin converting enzyme inhibitor medicines, which can be used to treat hypertension-complicated coronary diseases.
UsesIcariin has been used as a test material to investigate its, in vitro effect in promoting mouse hair follicle growth, which is assessed by vibrissae hair follicle (VHF) organ-culture model. It is also used as a hepatoprotective.
UsesIcariin has been used:in the preparation of topical treatment to determine its effects on the improvement of cutaneous wound healing in ratsto test its analgesic effects on lower back pain (LBP) in ratsas a potential treatment in osteoporosis condition in ratsto study its effects on palmitate (PA)-induced insulin resistance in skeletal muscle C2C12 myotubesas a neuroprotective agent to study its effects on amyloid-β (Aβ)-induced neuronal insulin resistance in human neuroblastoma SK-N-MC cells
General DescriptionIcariin is a prenylated flavonol and the major bioactive compound found in Epimedium herb.
Upstream & downstream products
Upstream raw materials
Related reactions
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Compound notes
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