Hesperidin Methyl Chalcone
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MedKoo CAT#: 330206

CAS#: 24292-52-2

Description: Hesperidin Methyl Chalcone is a derivative of the flavonoid hesperidin and is found in citrus fruits like oranges and grapefruit and is often used to reduce dark circles under the eyes.

Chemical Structure

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Hesperidin Methyl Chalcone
CAS# 24292-52-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 330206
Name: Hesperidin Methyl Chalcone
CAS#: 24292-52-2
Chemical Formula: C29H36O15
Exact Mass: 624.21
Molecular Weight: 624.592
Elemental Analysis: C, 55.77; H, 5.81; O, 38.42

Price and Availability

Size Price Availability Quantity
25g USD 350 2 Weeks
100g USD 950 2 Weeks
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Synonym: Hesperidin Methyl Chalcone; Hesperidin methylchalcone;

IUPAC/Chemical Name: (E)-1-(4-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-hydroxy-6-methoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-2-propen-1-one

InChi Key: FDHNLHLOJLLXDH-JIYHLSBYSA-N

InChi Code: InChI=1S/C29H36O15/c1-12-22(33)24(35)26(37)28(42-12)41-11-20-23(34)25(36)27(38)29(44-20)43-14-9-17(32)21(19(10-14)40-3)15(30)6-4-13-5-7-18(39-2)16(31)8-13/h4-10,12,20,22-29,31-38H,11H2,1-3H3/b6-4+/t12-,20+,22-,23+,24+,25-,26+,27+,28+,29+/m0/s1

SMILES Code: O=C(C1=C(OC)C=C(O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)O2)O)O)O)C=C1O)/C=C/C4=CC=C(OC)C(O)=C4

Appearance: Solid powder

Purity: >98% (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: >3 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:

Product Data:
Product Data
Instruction:
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Biological target: Hesperidin methylchalcone (Hesperidin methyl chalcone) inhibits oxidative stress, cytokine production and NF-κB activation.
In vitro activity: Ruscus/HMC (hesperidin methyl chalcone)/Vit C prepared in assay buffer and tested at concentrations of 0.1, 0.3, 1.0 and 3.0 mg/mL in triplicate in three independent experiments (n = 9) induced robust concentration-dependent calcium mobilization in LSMCs (lymphatic smooth muscle cells). When tested at concentrations of 1.0 and 3.0 mg/mL, Ruscus/HMC/Vit C induced a statistically significant LSMC contraction compared to control conditions (1118 ± 162, P < 0.01; 1685 ± 225, P < 0.001, respectively) with the same amplitude as that seen in response to 1 μM angiotensin II (1461 ± 338) for the two highest concentrations (Fig. 3). Reference: Microvasc Res. 2022 Jan;139:104274. https://pubmed.ncbi.nlm.nih.gov/34717967/
In vivo activity: HMC (hesperidin methyl chalcone) treatment inhibited the elevation of renal dysfunction markers induced by SDCF in a dose-dependent manner. HMC treatment restored the impaired plasmatic antioxidant status induced by SDFC, seen as increased FRAP and ABTS levels compared to the vehicle control, and inhibited lipid peroxidation levels, seen as a reduced concentration of TBARS. These results indicate HMC protects renal tissue from the toxic effects of SDFC. Further, HMC reduces systemic oxidative parameters in AKI mice, which reflects its potential antioxidant actions in response to increased free radical activity. Reference: Antioxidants (Basel). 2022 Jun 27;11(7):1261. https://pubmed.ncbi.nlm.nih.gov/35883752/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 80.05

Preparing Stock Solutions

The following data is based on the product molecular weight 624.59 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.

Recalculate based on batch purity %
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. Monjotin N, Tenca G. Lymphotonic activity of Ruscus extract, hesperidin methyl chalcone and vitamin C in human lymphatic smooth muscle cells. Microvasc Res. 2022 Jan;139:104274. doi: 10.1016/j.mvr.2021.104274. Epub 2021 Oct 27. PMID: 34717967. 2. Mansini AP, Peixoto E, Jin S, Richard S, Gradilone SA. The Chemosensory Function of Primary Cilia Regulates Cholangiocyte Migration, Invasion, and Tumor Growth. Hepatology. 2019 Apr;69(4):1582-1598. doi: 10.1002/hep.30308. Epub 2019 Mar 15. PMID: 30299561; PMCID: PMC6438749. 3. Bussmann AJC, Zaninelli TH, Saraiva-Santos T, Fattori V, Guazelli CFS, Bertozzi MM, Andrade KC, Ferraz CR, Camilios-Neto D, Casella AMB, Casagrande R, Borghi SM, Verri WA Jr. The Flavonoid Hesperidin Methyl Chalcone Targets Cytokines and Oxidative Stress to Reduce Diclofenac-Induced Acute Renal Injury: Contribution of the Nrf2 Redox-Sensitive Pathway. Antioxidants (Basel). 2022 Jun 27;11(7):1261. doi: 10.3390/antiox11071261. PMID: 35883752; PMCID: PMC9312103. 4. Guazelli CFS, Fattori V, Ferraz CR, Borghi SM, Casagrande R, Baracat MM, Verri WA Jr. Antioxidant and anti-inflammatory effects of hesperidin methyl chalcone in experimental ulcerative colitis. Chem Biol Interact. 2021 Jan 5;333:109315. doi: 10.1016/j.cbi.2020.109315. Epub 2020 Nov 7. PMID: 33171134
In vitro protocol: 1. Monjotin N, Tenca G. Lymphotonic activity of Ruscus extract, hesperidin methyl chalcone and vitamin C in human lymphatic smooth muscle cells. Microvasc Res. 2022 Jan;139:104274. doi: 10.1016/j.mvr.2021.104274. Epub 2021 Oct 27. PMID: 34717967. 2. Mansini AP, Peixoto E, Jin S, Richard S, Gradilone SA. The Chemosensory Function of Primary Cilia Regulates Cholangiocyte Migration, Invasion, and Tumor Growth. Hepatology. 2019 Apr;69(4):1582-1598. doi: 10.1002/hep.30308. Epub 2019 Mar 15. PMID: 30299561; PMCID: PMC6438749.
In vivo protocol: 1. Bussmann AJC, Zaninelli TH, Saraiva-Santos T, Fattori V, Guazelli CFS, Bertozzi MM, Andrade KC, Ferraz CR, Camilios-Neto D, Casella AMB, Casagrande R, Borghi SM, Verri WA Jr. The Flavonoid Hesperidin Methyl Chalcone Targets Cytokines and Oxidative Stress to Reduce Diclofenac-Induced Acute Renal Injury: Contribution of the Nrf2 Redox-Sensitive Pathway. Antioxidants (Basel). 2022 Jun 27;11(7):1261. doi: 10.3390/antiox11071261. PMID: 35883752; PMCID: PMC9312103. 2. Guazelli CFS, Fattori V, Ferraz CR, Borghi SM, Casagrande R, Baracat MM, Verri WA Jr. Antioxidant and anti-inflammatory effects of hesperidin methyl chalcone in experimental ulcerative colitis. Chem Biol Interact. 2021 Jan 5;333:109315. doi: 10.1016/j.cbi.2020.109315. Epub 2020 Nov 7. PMID: 33171134

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1: Mansini AP, Peixoto E, Jin S, Richard S, Gradilone SA. The Chemosensory Function of Primary Cilia Regulates Cholangiocyte Migration, Invasion, and Tumor Growth. Hepatology. 2019 Apr;69(4):1582-1598. doi: 10.1002/hep.30308. Epub 2019 Mar 15. PubMed PMID: 30299561; PubMed Central PMCID: PMC6438749.

2: Hernandez-Pigeon H, Garidou L, Galliano MF, Delga H, Aries MF, Duplan H, Bessou-Touya S, Castex-Rizzi N. Effects of dextran sulfate, 4-t-butylcyclohexanol, pongamia oil and hesperidin methyl chalcone on inflammatory and vascular responses implicated in rosacea. Clin Cosmet Investig Dermatol. 2018 Sep 7;11:421-429. doi: 10.2147/CCID.S168621. eCollection 2018. PubMed PMID: 30233225; PubMed Central PMCID: PMC6135068.

3: Zhao Y, Jiao Y, Wang L. Hesperidin methyl chalcone alleviates spinal tuberculosis in New Zealand white rabbits by suppressing immune responses. J Spinal Cord Med. 2018 Aug 20:1-8. doi: 10.1080/10790268.2018.1507805. [Epub ahead of print] PubMed PMID: 30124375.

4: Kakkos SK, Bouskela E, Jawien A, Nicolaides AN. New data on chronic venous disease: a new place for Cyclo 3® Fort. Int Angiol. 2018 Feb;37(1):85-92. doi: 10.23736/S0392-9590.17.03935-9. Epub 2017 Oct 23. Review. PubMed PMID: 29063748.

5: Jawien A, Bouskela E, Allaert FA, Nicolaïdes AN. The place of Ruscus extract, hesperidin methyl chalcone, and vitamin C in the management of chronic venous disease. Int Angiol. 2017 Feb;36(1):31-41. doi: 10.23736/S0392-9590.16.03788-3. Review. PubMed PMID: 28124877.

6: Martinez RM, Pinho-Ribeiro FA, Steffen VS, Caviglione CV, Pala D, Baracat MM, Georgetti SR, Verri WA, Casagrande R. Topical formulation containing hesperidin methyl chalcone inhibits skin oxidative stress and inflammation induced by ultraviolet B irradiation. Photochem Photobiol Sci. 2016 Apr;15(4):554-63. doi: 10.1039/c5pp00467e. Epub 2016 Mar 29. PubMed PMID: 27021784.

7: Allaert FA. Combination of Ruscus aculeatus extract, hesperidin methyl chalcone and ascorbic acid: a comprehensive review of their pharmacological and clinical effects and of the pathophysiology of chronic venous disease. Int Angiol. 2016 Apr;35(2):111-6. Review. PubMed PMID: 26928296.

8: Martinez RM, Pinho-Ribeiro FA, Steffen VS, Caviglione CV, Vignoli JA, Baracat MM, Georgetti SR, Verri WA Jr, Casagrande R. Hesperidin methyl chalcone inhibits oxidative stress and inflammation in a mouse model of ultraviolet B irradiation-induced skin damage. J Photochem Photobiol B. 2015 Jul;148:145-153. doi: 10.1016/j.jphotobiol.2015.03.030. Epub 2015 Apr 13. PubMed PMID: 25916506.

9: Andersen KE. Hesperidin methyl chalcone - a new cosmetic contact allergen. Contact Dermatitis. 2015 Jun;72(6):402-4. doi: 10.1111/cod.12383. Epub 2015 Mar 20. PubMed PMID: 25801999.

10: Pinho-Ribeiro FA, Hohmann MS, Borghi SM, Zarpelon AC, Guazelli CF, Manchope MF, Casagrande R, Verri WA Jr. Protective effects of the flavonoid hesperidin methyl chalcone in inflammation and pain in mice: role of TRPV1, oxidative stress, cytokines and NF-κB. Chem Biol Interact. 2015 Feb 25;228:88-99. doi: 10.1016/j.cbi.2015.01.011. Epub 2015 Jan 21. PubMed PMID: 25617481.

11: Guex JJ, Avril L, Enrici E, Enriquez E, Lis C, Taïeb C. Quality of life improvement in Latin American patients suffering from chronic venous disorder using a combination of Ruscus aculeatus and hesperidin methyl-chalcone and ascorbic acid (quality study). Int Angiol. 2010 Dec;29(6):525-32. PubMed PMID: 21173734.

12: Guex JJ, Enriquez Vega DM, Avril L, Boussetta S, Taïeb C. Assessment of quality of life in Mexican patients suffering from chronic venous disorder - impact of oral Ruscus aculeatus-hesperidin-methyl-chalcone-ascorbic acid treatment - 'QUALITY Study'. Phlebology. 2009 Aug;24(4):157-65. doi: 10.1258/phleb.2009.008066. PubMed PMID: 19620698.

13: Boyle P, Diehm C, Robertson C. Meta-analysis of clinical trials of Cyclo 3 Fort in the treatment of chronic venous insufficiency. Int Angiol. 2003 Sep;22(3):250-62. PubMed PMID: 14612852.

14: Beltramino R, Penenory A, Buceta AM. An open-label, randomized multicenter study comparing the efficacy and safety of Cyclo 3 Fort versus hydroxyethyl rutoside in chronic venous lymphatic insufficiency. Angiology. 2000 Jul;51(7):535-44. PubMed PMID: 10917578.

15: Beltramino R, Penenory A, Buceta AM. An open-label, randomised multicentre study comparing the efficacy and safety of CYCLO 3 FORT versus hydroxyethyl rutoside in chronic venous lymphatic insufficiency. Int Angiol. 1999 Dec;18(4):337-42. PubMed PMID: 10811525.

16: Cluzan RV, Alliot F, Ghabboun S, Pascot M. Treatment of secondary lymphedema of the upper limb with CYCLO 3 FORT. Lymphology. 1996 Mar;29(1):29-35. PubMed PMID: 8721977.

17: Rudofsky G. [Improving venous tone and capillary sealing. Effect of a combination of Ruscus extract and hesperidine methyl chalcone in healthy probands in heat stress]. Fortschr Med. 1989 Jun 30;107(19):52, 55-8. German. PubMed PMID: 2668140.

18: Silvestri S. A thin-layer chromatographic-fluorometric method for quantitative analysis of hesperidin methyl chalcone in parmaceuticals. Pharm Acta Helv. 1970 Jun;45(6):390-1. PubMed PMID: 5426104.

19: Gábor M, Antal A, Dirner Z. Effect of hesperidin-methyl-chalcone on capillary resistance in the internal organs of the guinea pig and the rat. Acta Physiol Acad Sci Hung. 1968;34(3):221-6. PubMed PMID: 5716503.

20: DONTAS AS, CHENOWETH MB. The effect of hesperidin methyl chalcone on the nervous control of the nictitating membrane. Arch Int Pharmacodyn Ther. 1952 Sep 1;91(1-2):202-10. English, Undetermined Language. PubMed PMID: 13008500.