Diosmin | CAS#520-27-4

Diosmin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 329594

CAS#: 520-27-4

Description: Diosmin, also known as Barosmin, is a flavonoid glycoside found in citrus fruits, hyssop, and rosemary. Diosmin pretreatment improves cardiac function and suppresses oxidative stress in rat heart after ischemia/reperfusion. Diosmin induces genotoxicity and apoptosis in DU145 prostate cancer cell line. Diosmin exhibits anti-hyperlipidemic effects in isoproterenol induced myocardial infarcted rats. Diosmin alleviates retinal edema by protecting the blood-retinal barrier and reducing retinal vascular permeability during ischemia/reperfusion injury. Diosmin protects against ethanol-induced hepatic injury via alleviation of inflammation and regulation of TNF-α and NF-κB activation.

Chemical Structure

Diosmin

CAS# 520-27-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329594
Name: Diosmin
CAS#: 520-27-4
Chemical Formula: C28H32O15
Exact Mass: 608.17
Molecular Weight: 608.549
Elemental Analysis: C, 55.26; H, 5.30; O, 39.44

Price and Availability

Size	Price	Availability
5g	USD 250	2 weeks
10g	USD 450	2 weeks
25g	USD 750	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Diosmin, Barosmin, 3’,5,7-Trihydroxy-4’-methoxyflavone 7-rutinoside.

IUPAC/Chemical Name: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key: GZSOSUNBTXMUFQ-YFAPSIMESA-N

InChi Code: InChI=1S/C28H32O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-8,10,19,21-30,32-37H,9H2,1-2H3/t10-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1

SMILES Code: OC1=C(C(C=C(C2=CC=C(OC)C(O)=C2)O3)=O)C3=CC(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]5[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O5)O4)=C1

Appearance: Solid powder

Purity: >90% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Diosmin is a semisynthetic flavonoid molecule derived from citrus d (modified hesperidin). It is an oral phlebotropic drug used in the treatment of venous disease, i.e., chronic venous insufficiency (CVI) including spider and varicose veins, leg swelling (edema), stasis dermatitis and venous ulcers. It is also used as a stand-alone or surgical adjunctive therapy in hemorrhoidal disease (HD).

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot# C22M02C17

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Diosmin is a flavonoid found in a variety of citrus fruits and also an agonist of the aryl hydrocarbon receptor (AhR).
In vitro activity:	Diosmetin, but not diosmin, directly inhibited cytochrome P450 1A1 (CYP1A1) activity in a noncompetitive manner in microsomes isolated from DMBA-treated cells, as assayed by ethyoxyresorufin-O-deethylase activity. Treatment of the cells with diosmin or diosmetin, on the other hand, caused a dose- and time-dependent increase in CYP1A1 activity in intact cells that was comparable to that induced by DMBA or by the aryl hydrocarbon benzo(a)pyrene. Reference: Cancer Res. 1998 Jul 1;58(13):2754-60. https://pubmed.ncbi.nlm.nih.gov/9661887/
In vivo activity:	In contrast, diosmin clearly protected against the retinal ischemic damage in the MD (model + diosmin) rat group, with normal patterns of organization in the outer nuclear and plexiform layers, except for a slight misalignment of the photoreceptors (Fig. 4). The thicknesses of the inner and outer retina and the GCL density in the MD group were significantly greater than those in the MV group (P<0.05, Table 1), confirming the protective effect of diosmin. Reference: J Ocul Pharmacol Ther. 2012 Oct;28(5):459-66. https://pubmed.ncbi.nlm.nih.gov/22509733/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	100.0	164.33

Preparing Stock Solutions

The following data is based on the product molecular weight 608.55 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Deng J, Zheng C, Hua Z, Ci H, Wang G, Chen L. Diosmin mitigates high glucose-induced endoplasmic reticulum stress through PI3K/AKT pathway in HK-2 cells. BMC Complement Med Ther. 2022 Apr 27;22(1):116. doi: 10.1186/s12906-022-03597-y. PMID: 35477428; PMCID: PMC9044681. 2. Ciolino HP, Wang TT, Yeh GC. Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity. Cancer Res. 1998 Jul 1;58(13):2754-60. PMID: 9661887. 3. Shaaban HH, Hozayen WG, Khaliefa AK, El-Kenawy AE, Ali TM, Ahmed OM. Diosmin and Trolox Have Anti-Arthritic, Anti-Inflammatory and Antioxidant Potencies in Complete Freund's Adjuvant-Induced Arthritic Male Wistar Rats: Roles of NF-κB, iNOS, Nrf2 and MMPs. Antioxidants (Basel). 2022 Aug 30;11(9):1721. doi: 10.3390/antiox11091721. PMID: 36139795; PMCID: PMC9495550. 4. Tong N, Zhang Z, Gong Y, Yin L, Wu X. Diosmin protects rat retina from ischemia/reperfusion injury. J Ocul Pharmacol Ther. 2012 Oct;28(5):459-66. doi: 10.1089/jop.2011.0218. Epub 2012 Apr 17. PMID: 22509733; PMCID: PMC3459007.
In vitro protocol:	1. Deng J, Zheng C, Hua Z, Ci H, Wang G, Chen L. Diosmin mitigates high glucose-induced endoplasmic reticulum stress through PI3K/AKT pathway in HK-2 cells. BMC Complement Med Ther. 2022 Apr 27;22(1):116. doi: 10.1186/s12906-022-03597-y. PMID: 35477428; PMCID: PMC9044681. 2. Ciolino HP, Wang TT, Yeh GC. Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity. Cancer Res. 1998 Jul 1;58(13):2754-60. PMID: 9661887.
In vivo protocol:	1. Shaaban HH, Hozayen WG, Khaliefa AK, El-Kenawy AE, Ali TM, Ahmed OM. Diosmin and Trolox Have Anti-Arthritic, Anti-Inflammatory and Antioxidant Potencies in Complete Freund's Adjuvant-Induced Arthritic Male Wistar Rats: Roles of NF-κB, iNOS, Nrf2 and MMPs. Antioxidants (Basel). 2022 Aug 30;11(9):1721. doi: 10.3390/antiox11091721. PMID: 36139795; PMCID: PMC9495550. 2. Tong N, Zhang Z, Gong Y, Yin L, Wu X. Diosmin protects rat retina from ischemia/reperfusion injury. J Ocul Pharmacol Ther. 2012 Oct;28(5):459-66. doi: 10.1089/jop.2011.0218. Epub 2012 Apr 17. PMID: 22509733; PMCID: PMC3459007.

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1: Imam F, Al-Harbi NO, Al-Harbi MM, Ansari MA, Zoheir KM, Iqbal M, Anwer MK, Al Hoshani AR, Attia SM, Ahmad SF. Diosmin downregulates the expression of T cell receptors, pro-inflammatory cytokines and NF-κB activation against LPS-induced acute lung injury in mice. Pharmacol Res. 2015 Dec;102:1-11. doi: 10.1016/j.phrs.2015.09.001. PubMed PMID: 26361726.

2: Neerati P, Bedada SK. Effect of diosmin on the intestinal absorption and pharmacokinetics of fexofenadine in rats. Pharmacol Rep. 2015 Apr;67(2):339-44. doi: 10.1016/j.pharep.2014.09.010. PubMed PMID: 25712660.

3: Russo R, Mancinelli A, Ciccone M, Terruzzi F, Pisano C, Severino L. Pharmacokinetic Profile of µSMIN Plus™, a new Micronized Diosmin Formulation, after Oral Administration in Rats. Nat Prod Commun. 2015 Sep;10(9):1569-72. PubMed PMID: 26594761.

4: Vrbata P, Berka P, Stránská D, Doležal P, Lázníček M. Electrospinning of diosmin from aqueous solutions for improved dissolution and oral absorption. Int J Pharm. 2014 Oct 1;473(1-2):407-13. doi: 10.1016/j.ijpharm.2014.07.017. PubMed PMID: 25066074.

5: Senthamizhselvan O, Manivannan J, Silambarasan T, Raja B. Diosmin pretreatment improves cardiac function and suppresses oxidative stress in rat heart after ischemia/reperfusion. Eur J Pharmacol. 2014 Aug 5;736:131-7. doi: 10.1016/j.ejphar.2014.04.026. PubMed PMID: 24769512.

6: Lewinska A, Siwak J, Rzeszutek I, Wnuk M. Diosmin induces genotoxicity and apoptosis in DU145 prostate cancer cell line. Toxicol In Vitro. 2015 Apr;29(3):417-25. doi: 10.1016/j.tiv.2014.12.005. PubMed PMID: 25499067.

7: Barreca D, Laganà G, Bruno G, Magazù S, Bellocco E. Diosmin binding to human serum albumin and its preventive action against degradation due to oxidative injuries. Biochimie. 2013 Nov;95(11):2042-9. doi: 10.1016/j.biochi.2013.07.014. PubMed PMID: 23886889.

8: Queenthy SS, John B. Diosmin exhibits anti-hyperlipidemic effects in isoproterenol induced myocardial infarcted rats. Eur J Pharmacol. 2013 Oct 15;718(1-3):213-8. doi: 10.1016/j.ejphar.2013.08.031. PubMed PMID: 24036254.

9: Hnátek L. [Therapeutic potential of micronized purified flavonoid fraction (MPFF) of diosmin and hesperidin in treatment chronic venous disorder]. Vnitr Lek. 2015 Sep;61(9):807-14. Review. Czech. PubMed PMID: 26465280.

10: Jain D, Bansal MK, Dalvi R, Upganlawar A, Somani R. Protective effect of diosmin against diabetic neuropathy in experimental rats. J Integr Med. 2014 Jan;12(1):35-41. doi: 10.1016/S2095-4964(14)60001-7. PubMed PMID: 24461593.

11: Milano G, Leone S, Fucile C, Zuccoli ML, Stimamiglio A, Martelli A, Mattioli F. Uncommon serum creatine phosphokinase and lactic dehydrogenase increase during diosmin therapy: two case reports. J Med Case Rep. 2014 Jun 16;8:194. doi: 10.1186/1752-1947-8-194. PubMed PMID: 24934505; PubMed Central PMCID: PMC4070635.

12: Tong N, Zhang Z, Zhang W, Qiu Y, Gong Y, Yin L, Qiu Q, Wu X. Diosmin alleviates retinal edema by protecting the blood-retinal barrier and reducing retinal vascular permeability during ischemia/reperfusion injury. PLoS One. 2013 Apr 24;8(4):e61794. doi: 10.1371/journal.pone.0061794. PubMed PMID: 23637907; PubMed Central PMCID: PMC3634841.

13: Bogucka-Kocka A, Woźniak M, Feldo M, Kockic J, Szewczyk K. Diosmin--isolation techniques, determination in plant material and pharmaceutical formulations, and clinical use. Nat Prod Commun. 2013 Apr;8(4):545-50. Review. PubMed PMID: 23738475.

14: Tahir M, Rehman MU, Lateef A, Khan R, Khan AQ, Qamar W, Ali F, O'Hamiza O, Sultana S. Diosmin protects against ethanol-induced hepatic injury via alleviation of inflammation and regulation of TNF-α and NF-κB activation. Alcohol. 2013 Mar;47(2):131-9. doi: 10.1016/j.alcohol.2012.12.010. PubMed PMID: 23419394.

15: Tong N, Zhang Z, Gong Y, Yin L, Wu X. Diosmin protects rat retina from ischemia/reperfusion injury. J Ocul Pharmacol Ther. 2012 Oct;28(5):459-66. PubMed PMID: 22509733; PubMed Central PMCID: PMC3459007.

16: Freag MS, Elnaggar YS, Abdallah OY. Development of novel polymer-stabilized diosmin nanosuspensions: in vitro appraisal and ex vivo permeation. Int J Pharm. 2013 Sep 15;454(1):462-71. doi: 10.1016/j.ijpharm.2013.06.039. PubMed PMID: 23830765.

17: Dung TD, Day CH, Binh TV, Lin CH, Hsu HH, Su CC, Lin YM, Tsai FJ, Kuo WW, Chen LM, Huang CY. PP2A mediates diosmin p53 activation to block HA22T cell proliferation and tumor growth in xenografted nude mice through PI3K-Akt-MDM2 signaling suppression. Food Chem Toxicol. 2012 May;50(5):1802-10. doi: 10.1016/j.fct.2012.01.021. PubMed PMID: 22289577.

18: Tahir M, Rehman MU, Lateef A, Khan AQ, Khan R, Qamar W, O'Hamiza O, Ali F, Hasan SK, Sultana S. Diosmin abrogates chemically induced hepatocarcinogenesis via alleviation of oxidative stress, hyperproliferative and inflammatory markers in murine model. Toxicol Lett. 2013 Jul 18;220(3):205-18. doi: 10.1016/j.toxlet.2013.04.004. PubMed PMID: 23665045.

19: Dholakiya SL, Benzeroual KE. Protective effect of diosmin on LPS-induced apoptosis in PC12 cells and inhibition of TNF-α expression. Toxicol In Vitro. 2011 Aug;25(5):1039-44. doi: 10.1016/j.tiv.2011.04.003. PubMed PMID: 21477647.

20: Giannini I, Amato A, Basso L, Tricomi N, Marranci M, Pecorella G, Tafuri S, Pennisi D, Altomare DF. Flavonoids mixture (diosmin, troxerutin, hesperidin) in the treatment of acute hemorrhoidal disease: a prospective, randomized, triple-blind, controlled trial. Tech Coloproctol. 2015 Jun;19(6):339-45. doi: 10.1007/s10151-015-1302-9. Erratum in: Tech Coloproctol. 2015 Oct;19(10):665-6. PubMed PMID: 25893991.

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