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Icariin

Applications Description References
Product Name
Icariin
CAS No.
489-32-7
Chemical Name
Icariin
Synonyms
epimedium extract;Horny goat weed extract;ICARIN;ICARRIN;Icraiin;ICARIINE;Epimedium Extract Icariin;4H-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;yyhxwz
CBNumber
CB7345038
Molecular Formula
C33H40O15
Formula Weight
676.66
MOL File
489-32-7.mol
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Icariin Property

Melting point:
223-225 ºC
alpha 
D15 -87.09° (in pyridine)
Boiling point:
948.5±65.0 °C(Predicted)
Density 
1.55
RTECS 
DJ2980500
storage temp. 
2-8°C
solubility 
DMSO: soluble50mg/mL, clear, colorless to dark yellow
form 
Powder
pka
5.90±0.40(Predicted)
color 
light yellow to yellow
λmax
350nm(MeOH)(lit.)
Merck 
14,3617
Stability:
Light Sensitive
InChIKey
TZJALUIVHRYQQB-XLRXWWTNSA-N
LogP
1.736 (est)
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Safety

Safety Statements 
24/25
WGK Germany 
3
HS Code 
29389090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHL89714
Product name
Icariin
Purity
phyproof? Reference Substance
Packaging
10MG
Price
$372
Updated
2024/03/01
Sigma-Aldrich
Product number
I1286
Product name
Icariin
Purity
≥94% (HPLC)
Packaging
1g
Price
$949
Updated
2024/03/01
Sigma-Aldrich
Product number
56601
Product name
Icariin
Purity
analytical standard
Packaging
25mg
Price
$366
Updated
2024/03/01
TCI Chemical
Product number
I0862
Product name
Icariin
Purity
>96.0%(HPLC)
Packaging
1g
Price
$386
Updated
2024/03/01
TCI Chemical
Product number
I0862
Product name
Icariin
Purity
>96.0%(HPLC)
Packaging
200mg
Price
$118
Updated
2024/03/01
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Icariin Chemical Properties,Usage,Production

Applications

Icariin inhibits the ROS-dependent JNK and p38 pathways.

Description

Icariin 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.

References

[1] K. M. Chen, B. F. Ge, H. P. Ma, X. Y. Liu, M. H. Bai, Y, Wang (2005) Icariin, a flavonoid from the herb Epimedium enhances the osteogenic differentiation of rat primary bone marrow stromal cells, 60, 939-942
[2] Patent CN 1199647C “Application of icariin in preparation of medicine for preventing and treating sexual dysfunction”
[3] Patent CN 104739851 A “New application of icariin, or icariin derivatives or icariin salt”

Chemical Properties

Light yellow to yellow solid

Uses

Icariin 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.

Uses

Icariin has been used:

  • in the preparation of topical treatment to determine its effects on the improvement of cutaneous wound healing in rats
  • to test its analgesic effects on lower back pain (LBP) in rats
  • as a potential treatment in osteoporosis condition in rats
  • to study its effects on palmitate (PA)-induced insulin resistance in skeletal muscle C2C12 myotubes
  • as a neuroprotective agent to study its effects on amyloid-β (Aβ)-induced neuronal insulin resistance in human neuroblastoma SK-N-MC cells

Definition

ChEBI: Icariin is a member of the class of flavonols that is kaempferol which is substituted at position 8 by a 3-methylbut-2-en-1-yl group and in which the hydroxy groups at positions 3, 4', and 7 have been converted to the corresponding 6-deoxy-alpha-L-mannopyranoside, methyl ether, and beta-D-glucopyranoside, respectively. A phoshphodiesterase-5 inhibitor, it is obtained from several species of plants in the genus Epimedium and is thought to be the main active ingredient of the Chinese herbal medicine Herba Epimedii (yinyanghuo). It has a role as a bone density conservation agent, a phytoestrogen, an EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor and an antioxidant. It is a glycosyloxyflavone and a member of flavonols.

General Description

Icariin is a prenylated flavonol and the major bioactive compound found in Epimedium herb.

Biological Activity

icariin exhibits inhibitory effects on cgmp-specific phosphodiesterase pde5 and camp-specific phosphodiesterase pde4 activities. phosphodiesterase (pde) is a crucial regulator of camp/pka signaling. pdes are encoded by 21 genes which can be sdivided into 11 families according to the substrate specificities and subcellular localization. pdes are widely expressed in neurons. pde5 has been implicated in regulating some physiological processes such as smooth muscle relaxation and neuronal survival. pde4 has been associated with the darpp-32 signaling pathway and dopaminergic neurotransmission [1].

Biochem/physiol Actions

Icariin is a potent neuroprotective agent in neurodegenerative disorders and other disorders affecting the nervous system. It elicits anti-aging properties in unfertilized oocytes against age-related damage. Icariin exerts anti-inflammatory and antifibrotic properties aiding protection in chronic kidney disease (CKD)-associated renal fibrosis in mouse model. It also serves as an excellent antidiabetic and anti-atherosclerotic agent. Icariin is an excellent anti-cancer agent.

Mechanism of action

Icariin is known as an indicative constituent of the Epimedium genus, which has been commonly used in Chinese herbal medicine to enhance treat impotence and improve sexual function, as well as for several other indications for over 2000 years. Icariside II is a intestinal metabolite of icariin. Their inhibition profile are different. Icaritin is a potent inhibitor of UGT1A7 and UGT1A9 but icariside II is a potent inhibitor of UGT1A4, UGT1A7, UGT1A9, and UGT2B7.

in vitro

icariin inhibited the activity of pde5 and pde4 in a dose- andconcentration-dependent manner. the ic50of icariin on pde5 was 0.43 μm and the ic50 on pde4 was 73.50 μm. icariin showed a selective inhibitory effect on cgmp-specific pde5 compared to camp-specific pde4 [2].icariincould also enhance the osteogenic differentiation of rat primary bone marrow stromal cells [3].

in vivo

in castrated rats, a 4-week oral administration of icariinat 1 mg/kg/day and 5 mg/kg/day improved the erectile function and increased nnos and inos expression [4].icariin also showed its effect on stimulating angiogenesis in human endothelial cells [5].

References

nishi a, kuroiwa m, miller d b, et al. distinct roles of pde4 and pde10a in the regulation of camp/pka signaling in the striatum[j]. the journal of neuroscience, 2008, 28(42): 10460-10471.xin z c, kim e k, lin c s, et al. effects of icariin on cgmp-specific pde5 and camp-specific pde4 activities[j]. asian journal of andrology, 2003, 5(1): 15-18.chen k m, ge b f, ma h p, et al. icariin, a flavonoid from the herb epimedium enhances the osteogenic differentiation of rat primary bone marrow stromal cells[j]. die pharmazie-an international journal of pharmaceutical sciences, 2005, 60(12): 939-942.liu w j, xin z c, xin h, et al. effects of icariin on erectile function and expression of nitric oxide synthase isoforms in castrated rats[j]. asian journal of andrology, 2005, 7(4): 381-388.chung b h, kim j d, kim c k, et al. icariin stimulates angiogenesis by activating the mek/erk-and pi3k/akt/enos-dependent signal pathways in human endothelial cells[j]. biochemical and biophysical research communications, 2008, 376(2): 404-408.

Icariin Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Icariin manufacturers

Dorne Chemical Technology co. LTD
Product
Icariin 489-32-7
Price
US $10.00/ASSAYS
Min. Order
1ASSAYS
Purity
99%
Supply Ability
100kg
Release date
2024-03-26
Sinoway Industrial co., ltd.
Product
Epimedium P.E. 489-32-7
Price
US $0.00/Kg/Bag
Min. Order
2Kg/Bag
Purity
Icariin ≥ 98% %
Supply Ability
20 tons
Release date
2024-04-09
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Icariin Powder 489-32-7
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-14

489-32-7, IcariinRelated Search:

Yeast extract Ginkgo biloba extract ISATIDS Epimedin A Grape Seed Extract Apigenin D-(-)-Salicin Matrine Epimedium Extract Resveratrol NOR-ICARITIN Anhydroicaritin Icariside I epimedoside A Motherwort Herb P.E Icaritin 4H-1-Benzopyran-4-one, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-8-(3-hydroxy-3-methylbutyl)-2-(4-methoxyphenyl)- Epimedium polysaccharide

  • Horny goat weed extract
  • ICARIINE
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  • Icariin Min 90% SynonyMs 3-[(6-Deoxy-alpha-L-Mannopyranosyl)oxy]-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-Methoxyphenyl)-8-(3-Methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
  • 4H-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)-
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  • ICARIIN, 98+% BY HPLC
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  • Icariil
  • ICARIIN(P)
  • Shorthorned Epimedium P.E
  • ICARIDININSECTREPELLENT
  • ICARIN
  • Icariin
  • Herba epimedium extract
  • Icariin cas:489-32-7
  • Icariin 489-32-7
  • Horny goat weed extrac
  • Iicariin
  • Icariin Powder
  • yyhxwz
  • 2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-
  • 4H-1-Benzopyran-4-one,3-[(6-deoxy-α-L-mannopy
  • ranosyl)oxy]-7-(β-D-glucopyranosyloxy)-5-hydroxy-
  • 3-(6-Deoxy-α-L-mannopyranosyloxy)-7-(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-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-buten-1-yl)-4H-1-benzopyran-4-one
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  • Icariin 5%,10%,20%,50%,98%
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  • 98% Icariin Epimedium Extract Powder
  • 3-[4,5-Dihydroxy-6-methyl-3-(
  • 5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
  • Icariin USP/EP/BP
  • Icariin-Epimedium Extract
  • Barrenwort P.E