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Eriocitrin

Cat No.:V20689 Purity: ≥98%
Eriocitrin is a natural flavonoid extracted from lemons that is a potent antioxidant.
Eriocitrin
Eriocitrin Chemical Structure CAS No.: 13463-28-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Eriocitrin is a natural flavonoid extracted from lemons that is a potent antioxidant. Eriocitrin suppresses the proliferation/growth of liver cancer/tumor cells by upregulating p53, cyclin A, cyclin D3 and CDK6 to arrest the cell cycle in the S phase. Eriocitrin triggers apoptosis by activating intrinsic signaling pathways involving mitochondria.
Eriocitrin (Eriodictyol-7-O-rutinoside) is a naturally occurring flavanone glycoside found predominantly in lemon (Citrus limon) and lime fruits. It is a potent antioxidant flavonoid with a 3′,4′-dihydroxy substituted B-ring. Eriocitrin has been studied for its lipid-lowering, anti-inflammatory, and anticancer properties. It is characterized by a distinct 50:50 (2S:2R) diastereomeric ratio that serves as a quality control fingerprint for lemon-derived authenticity.
Biological Activity I Assay Protocols (From Reference)
Targets
Eriocitrin exhibits multiple biological activities through various mechanisms. It is a powerful antioxidative flavonoid that prevents oxidative damages. Eriocitrin inhibits the proliferation of hepatocellular carcinoma cell lines by arresting the cell cycle in S phase through up-regulation of p53, cyclin A, cyclin D3, and CDK6. It also exhibits lipid-lowering effects in rat models of high-fat diet. The compound inhibits lipid peroxidation in cell-free assays.
ln Vitro
HepG2 and Huh7, two liver cancer cell lines, are inhibited in their ability to proliferate and form foci by erynocitrin (25–75 μM; 24 hours), which also disrupts the cell cycle in the S phase (5–10 μM; 24 hours) [1]. In HepG2 cells, eriocitrin (25–75 μM; 12 hours) increases the levels of p53, cyclin A, cyclin D3, and CDK6 [1]. Through the activation of intrinsic signaling pathways connected to mitochondria, eriocirin (25-75 μM; 48 hours) causes apoptosis [1].
In vitro, eriocitrin is a powerful antioxidative flavonoid that prevents oxidative damages. It inhibits the proliferation of hepatocellular carcinoma cell lines by arresting the cell cycle in S phase through up-regulation of p53, cyclin A, cyclin D3, and CDK6. The compound inhibits lipid peroxidation in cell-free assays when used at a concentration of 10 µM. It exhibits antioxidant, anti-inflammatory, and antitumor activities in various cell-based assays.
ln Vivo
Acute kidney injury (AKI) caused by ischemia-reperfusion (IR) in rats is lessened by eriocirin (10–60 mg/kg; intraperitoneal injection; once daily, from the day of modeling until the end of the experiment) and renal tissue cell apoptosis is decreased, altering the renal inflammatory response and oxidative stress [2].
In vivo, eriocitrin has lipid-lowering effects in rats on a high-fat and high-cholesterol diet. It demonstrates 33% higher Cmax and 43% greater AUC than hesperidin, ensuring consistent systemic exposure. The compound shows 8-fold higher composite antioxidant potency (APC) and strong H₂O₂ scavenging activity. These findings support its potential as a dietary supplement for managing lipid disorders and oxidative stress.
Enzyme Assay
Non-cellular assays for eriocitrin involve assessing its antioxidant activity using cell-free systems. The compound's ability to scavenge free radicals can be evaluated using DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)), or FRAP (ferric reducing antioxidant power) assays. Its ability to inhibit lipid peroxidation can be measured using the thiobarbituric acid reactive substances (TBARS) assay.
Cell Assay
In vitro cellular assays for eriocitrin involve treating hepatocellular carcinoma cell lines (e.g., HepG2, Huh7) with the compound and assessing cell viability, proliferation, and cell cycle progression. Cell viability is measured using MTT or CellTiter-Glo® assays. Cell cycle analysis is performed by flow cytometry using propidium iodide staining. The expression of cell cycle regulatory proteins (p53, cyclin A, cyclin D3, CDK6) is assessed by Western blotting or qPCR.
Animal Protocol
In vivo animal experiments with eriocitrin are conducted in rat models of high-fat diet-induced hyperlipidemia. Rats are fed a high-fat and high-cholesterol diet and treated with eriocitrin via oral administration. Serum lipid levels (total cholesterol, triglycerides, LDL-C, HDL-C) are measured. Liver histology is examined to assess hepatic steatosis. The compound's lipid-lowering effects and antioxidant activity are evaluated.
ADME/Pharmacokinetics
Eriocitrin has a molecular weight of 596.5 and a molecular formula of C₂₇H₃₂O₁₅. It is a solid powder with a purity of ≥98%. The compound is soluble in DMSO. It is typically stored dry, dark, and at 0-4°C for short-term storage (days to weeks) or at -20°C for long-term storage (months to years). The compound is stable under recommended storage conditions.
Toxicity/Toxicokinetics
Eriocitrin is a research compound for laboratory use only and is not approved for human therapeutic use. As a natural flavonoid, it is generally considered to have low toxicity. Standard laboratory safety precautions should be followed when handling the compound. It may cause skin, eye, and respiratory irritation. Appropriate personal protective equipment should be used.
References

[1]. Eriocitrin from lemon suppresses the proliferation of human hepatocellular carcinoma cells through inducing apoptosis and arresting cell cycle. Cancer Chemother Pharmacol. 2016 Dec;78(6):1143-1150.

[2]. Eriocitrin attenuates ischemia reperfusion-induced oxidative stress and inflammation in rats with acute kidney injury by regulating the dual-specificity phosphatase 14 (DUSP14)-mediated Nrf2 and nuclear factor-κB (NF-κB) pathways. Ann Transl Med. 2021 Feb;9(4):350.

Additional Infomation
Eriocitrin is a disaccharide derivative formed by linking sennaol to a 6-O-(α-L-rhamnosyl)-β-D-glucopyranosyl moiety at the 7-position via a glycosidic bond. It possesses antioxidant properties. Eriocitrin is a disaccharide derivative belonging to the classes of 3'-hydroxyflavanones, trihydroxyflavanones, flavanone glycosides, 4'-hydroxyflavanones, and rutin glycosides. Its function is related to sennaol. Eriocitrin has been reported to be present in Succina, Reticulata, and other organisms with relevant data.
Eriocitrin (CAS 13463-28-0) is a naturally occurring flavanone glycoside found in lemons with powerful antioxidant activity. It inhibits hepatocellular carcinoma cell proliferation by arresting the cell cycle in S phase. Eriocitrin has lipid-lowering effects in rat models of high-fat diet. The compound shows 33% higher Cmax and 43% greater AUC than hesperidin. It is available from various commercial suppliers for research applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C27H32O15
Molecular Weight
596.5340
Exact Mass
596.174
CAS #
13463-28-0
PubChem CID
83489
Appearance
Light yellow to yellow solid powder
Density
1.7±0.1 g/cm3
Boiling Point
956.9±65.0 °C at 760 mmHg
Melting Point
161-190ºC
Flash Point
317.0±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.727
LogP
1.47
Hydrogen Bond Donor Count
9
Hydrogen Bond Acceptor Count
15
Rotatable Bond Count
6
Heavy Atom Count
42
Complexity
924
Defined Atom Stereocenter Count
11
SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O)O
InChi Key
OMQADRGFMLGFJF-MNPJBKLOSA-N
InChi Code
InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
Chemical Name
(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~167.64 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.49 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (3.49 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.6764 mL 8.3818 mL 16.7636 mL
5 mM 0.3353 mL 1.6764 mL 3.3527 mL
10 mM 0.1676 mL 0.8382 mL 1.6764 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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