Synonym
Hesperetin; (S)-Hesperetin; (–)-Hesperetin; (–)-3',5,7-Trihydroxy-4'-methoxyflavanone; NSC 57654; NSC57654; NSC-57654
IUPAC/Chemical Name
(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
InChi Key
AIONOLUJZLIMTK-AWEZNQCLSA-N
InChi Code
InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
SMILES Code
COC1=C(C=C(C=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)O)O)O
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, not in water
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
Biological target:
Hesperetin is a natural flavanone, and acts as a potent and broad-spectrum inhibitor against human UGT activity.
In vitro activity:
As shown in Figure 2A, the treatment of GL261 cells with HSP resulted in shrunken and densely stained nuclei, which suggested that HSP (hesperetin) induced apoptosis. In addition, HSP increased the apoptosis rate in a concentration-dependent manner (Figure 2B,2C), with 200 µM of HSP increasing the apoptosis rate significantly (P<0.05). Finally, 400 µM of HSP induced apoptosis in 22.73% (SD 1.73%) of GL261 cells, while 800 µM of HSP induced apoptosis in 27.50% (SD 2.56%) of GL261 cells (Figure 2C).
Reference: Transl Cancer Res. 2022 Jun;11(6):1781-1794. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9273669/
In vivo activity:
Co-administration of hesperetin with sorafenib (1.3±0.12) significantly reduced these protein levels compared with the other mice groups (1.037±0.063), (1.12±0.018), (4.1±0.55) respectively as shown in (Fig 2). The administration of sorafenib alone resulted in a significant increase in cardiac TLR4 protein (3±0.2). In contrast, the group treated with the combination of sorafenib and hesperetin exhibited significantly lower levels of TLR4 protein (1.4±0.03) (Fig 2).
Reference: PLoS One. 2022 Aug 9;17(8):e0271631. https://pubmed.ncbi.nlm.nih.gov/35944026/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
99.25 |
| DMSO |
63.7 |
210.62 |
| DMSO:PBS (pH 7.2) (1:8) |
0.5 |
1.65 |
| Ethanol |
1.5 |
4.96 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
302.28
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. Cheng Q, Mao L, Huang H, Tang L, Jiang H, Zhang Y, Mu Q. Hesperetin ameliorates glioblastoma by inhibiting proliferation, inducing apoptosis, and suppressing metastasis. Transl Cancer Res. 2022 Jun;11(6):1781-1794. doi: 10.21037/tcr-22-1497. PMID: 35836521; PMCID: PMC9273669.
2. Nishino S, Fujiki Y, Sato T, Kato Y, Shirai R, Oizumi H, Yamamoto M, Ohbuchi K, Miyamoto Y, Mizoguchi K, Yamauchi J. Hesperetin, a Citrus Flavonoid, Ameliorates Inflammatory Cytokine-Mediated Inhibition of Oligodendroglial Cell Morphological Differentiation. Neurol Int. 2022 May 31;14(2):471-487. doi: 10.3390/neurolint14020039. PMID: 35736620; PMCID: PMC9230394.
3. Zaafar D, Khalil HMA, Rasheed RA, Eltelbany RFA, Zaitone SA. Hesperetin mitigates sorafenib-induced cardiotoxicity in mice through inhibition of the TLR4/NLRP3 signaling pathway. PLoS One. 2022 Aug 9;17(8):e0271631. doi: 10.1371/journal.pone.0271631. PMID: 35944026; PMCID: PMC9362940.
4. Yeh CH, Shen ZQ, Wang TW, Kao CH, Teng YC, Yeh TK, Lu CK, Tsai TF. Hesperetin promotes longevity and delays aging via activation of Cisd2 in naturally aged mice. J Biomed Sci. 2022 Jul 24;29(1):53. doi: 10.1186/s12929-022-00838-7. PMID: 35871686; PMCID: PMC9310407.
In vitro protocol:
1. Cheng Q, Mao L, Huang H, Tang L, Jiang H, Zhang Y, Mu Q. Hesperetin ameliorates glioblastoma by inhibiting proliferation, inducing apoptosis, and suppressing metastasis. Transl Cancer Res. 2022 Jun;11(6):1781-1794. doi: 10.21037/tcr-22-1497. PMID: 35836521; PMCID: PMC9273669.
2. Nishino S, Fujiki Y, Sato T, Kato Y, Shirai R, Oizumi H, Yamamoto M, Ohbuchi K, Miyamoto Y, Mizoguchi K, Yamauchi J. Hesperetin, a Citrus Flavonoid, Ameliorates Inflammatory Cytokine-Mediated Inhibition of Oligodendroglial Cell Morphological Differentiation. Neurol Int. 2022 May 31;14(2):471-487. doi: 10.3390/neurolint14020039. PMID: 35736620; PMCID: PMC9230394.
In vivo protocol:
1. Zaafar D, Khalil HMA, Rasheed RA, Eltelbany RFA, Zaitone SA. Hesperetin mitigates sorafenib-induced cardiotoxicity in mice through inhibition of the TLR4/NLRP3 signaling pathway. PLoS One. 2022 Aug 9;17(8):e0271631. doi: 10.1371/journal.pone.0271631. PMID: 35944026; PMCID: PMC9362940.
2. Yeh CH, Shen ZQ, Wang TW, Kao CH, Teng YC, Yeh TK, Lu CK, Tsai TF. Hesperetin promotes longevity and delays aging via activation of Cisd2 in naturally aged mice. J Biomed Sci. 2022 Jul 24;29(1):53. doi: 10.1186/s12929-022-00838-7. PMID: 35871686; PMCID: PMC9310407.
1: Yang LJ, Xia S, Ma SX, Zhou SY, Zhao XQ, Wang SH, Li MY, Yang XD. Host-guest system of hesperetin and β-cyclodextrin or its derivatives: Preparation, characterization, inclusion mode, solubilization and stability. Mater Sci Eng C Mater Biol Appl. 2016 Feb 1;59:1016-24. doi: 10.1016/j.msec.2015.10.037. Epub 2015 Oct 23. PubMed PMID: 26652460.
2: de Souza VT, de Franco ÉP, de Araújo ME, Messias MC, Priviero FB, Frankland Sawaya AC, de Oliveira Carvalho P. Characterization of the antioxidant activity of aglycone and glycosylated derivatives of hesperetin: an in vitro and in vivo study. J Mol Recognit. 2016 Feb;29(2):80-7. doi: 10.1002/jmr.2509. Epub 2015 Sep 15. PubMed PMID: 26370929.
3: Wei L, Deng W, Cheng Z, Guo H, Wang S, Zhang X, He Y, Tang Q. Effects of hesperetin on platelet-derived growth factor-BB-induced pulmonary artery smooth muscle cell proliferation. Mol Med Rep. 2016 Jan;13(1):955-60. doi: 10.3892/mmr.2015.4625. Epub 2015 Nov 30. PubMed PMID: 26647836.
4: Shen C, Chen R, Qian Z, Huang C, Meng X, Ma T, Chen Z, Huang X, Li L, Zang H, Li J. A HPLC-MS/MS method for the quantitation of free, conjugated, and total HDND-7, a novel hesperetin derivative, in rat plasma and tissues: Application to the pharmacokinetic and tissue distribution study. J Pharm Biomed Anal. 2016 Jan 25;118:149-60. doi: 10.1016/j.jpba.2015.10.031. Epub 2015 Oct 27. PubMed PMID: 26551533.
5: Wang QQ, Shi JB, Chen C, Huang C, Tang WJ, Li J. Hesperetin derivatives: Synthesis and anti-inflammatory activity. Bioorg Med Chem Lett. 2016 Mar 1;26(5):1460-5. doi: 10.1016/j.bmcl.2016.01.058. Epub 2016 Jan 22. PubMed PMID: 26848111.
