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Lavandoside

Alias: Lavandoside; 2-Propenoic acid, 3-[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]-, (2E)-; (E)-4-Hydroxy-3-methoxycinnamic acid 4-O-; A-D-glucopyranoside; (2E)-3-[4-(beta-D-Glucopyranosyloxy)-3-methoxyphenyl]-2-propenoic acid; (E)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid; Ferulic acid 4-glucoside;
Cat No.:V64392 Purity: ≥98%
Lavandoside is a naturally occurring and bioactive compound found in lavender flowers.
Lavandoside
Lavandoside Chemical Structure CAS No.: 117405-51-3
Product category: Plants
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description
Lavandoside is a naturally occurring and bioactive compound found in lavender flowers.
Lavandoside (CAS 117405-51-3) is a naturally occurring phenylpropanoid glycoside, structurally defined as trans-ferulic acid 4-O-β-D-glucopyranoside. It is also specifically identified as (E)-4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside. The compound has the molecular formula C₁₆H₂₀O₉ and a molecular weight of 356.33 g/mol. Lavandoside can be isolated from lavender (Lavandula spica) and is also derived from Helianthemum ruficomum. The compound functions as an ABTS⁺ free radical scavenger and a moderate inhibitor of xanthine oxidase (XO). Lavandoside exerts its antioxidant and potential anti-inflammatory effects by directly scavenging free radicals and inhibiting XO activity, a mechanism related to the hydroxyl groups in its molecular structure. The compound is used in the development of natural antioxidants and in research on oxidative stress-related diseases and inflammation-related diseases.
Biological Activity I Assay Protocols (From Reference)
Targets
Natural product
Lavandoside functions as a moderate inhibitor of xanthine oxidase (XO). It also acts as an ABTS⁺ free radical scavenger, exerting its effects through direct radical neutralization. The compound's antioxidant and potential anti-inflammatory effects are attributed to the hydroxyl groups in its molecular structure. Lavandoside modulates inflammatory pathways, thereby reducing inflammation. The compound's targets include antioxidant pathways and xanthine oxidase activity, with its mechanism related to the hydroxyl groups in its molecular structure. It has also been noted to have antibacterial activity.
ln Vitro
The new natural compound lavandoside with the structure ferulic acid 4-O-β-D-glucopyranoside was isolated by column chromatography over silica gel and polyamide from the extract of Lavandula spica flowers. The chemical structure of lavandoside was established using UV, NMR, and mass spectra and chemical transformations[1].
Lavandoside demonstrates moderate inhibition of xanthine oxidase (XO). In LPS-induced macrophages, it inhibits nitric oxide (NO) production with an IC₅₀ of 71.6 μM. The compound exhibits ABTS⁺ free radical scavenging activity, indicating its potential as a natural antioxidant. Its mechanism involves direct scavenging of free radicals and inhibition of XO activity. Lavandoside acts as a reducing agent, scavenging free radicals and reducing oxidative stress in cells. It also has potential anti-inflammatory effects through its modulation of xanthine oxidase activity, attributed to the hydroxyl groups within its structure.
ln Vivo
No detailed in vivo studies have been reported for Lavandoside. Its biological activities have been primarily characterized through in vitro assays, and no animal model data are currently available in the published literature. The compound is isolated from lavender and can be used in the development of natural antioxidants and in research on oxidative stress-related diseases and inflammation-related diseases.
Enzyme Assay
Lavandoside's xanthine oxidase inhibitory activity can be assessed using a standard spectrophotometric assay measuring uric acid production from xanthine substrate. ABTS⁺ radical scavenging activity is evaluated using the ABTS decolorization assay, where the compound's ability to reduce the ABTS radical cation is measured spectrophotometrically at 734 nm. NO inhibition is assessed in LPS-stimulated macrophage cultures using the Griess assay. The antioxidant power of Lavandoside has been evaluated by HPLC-ABTS⁺, TEAC and ORAC assays. The compound's antioxidant activity has been demonstrated through these established biochemical assays.
Cell Assay
The cellular activity of Lavandoside is evaluated in mouse RAW264.7 macrophages stimulated with lipopolysaccharide (LPS) to induce nitric oxide production. Cells are treated with Lavandoside for 24 hours, after which NO levels in the culture supernatant are measured using the Griess assay. The compound shows an IC₅₀ of 71.6 μM for inhibiting LPS-induced NO production. This assay demonstrates the compound's anti-inflammatory activity in mouse RAW264.7 cells. The cellular model is used to assess the compound's ability to modulate inflammatory responses through the inhibition of nitric oxide production.
Animal Protocol
No in vivo animal experimental protocols have been documented for Lavandoside. As a natural product research compound, its primary evaluation has been limited to cell-based and biochemical assays. The compound is used in the development of natural antioxidants and in research on oxidative stress-related diseases and inflammation-related diseases, but these applications are primarily studied in vitro.
ADME/Pharmacokinetics
Pharmacokinetic data for Lavandoside have not been reported. As a glycoside, it may undergo deglycosylation in the gastrointestinal tract, potentially affecting its oral bioavailability and systemic exposure. The compound's pharmacokinetic properties have not been characterized in the published literature.
Toxicity/Toxicokinetics
No toxicity data have been reported for Lavandoside. As a naturally occurring phenolic glycoside found in lavender, it is generally considered to have a favorable safety profile, though systematic toxicological evaluation has not been performed. The compound is classified as a natural product with antioxidant and anti-inflammatory potential.
References

[1]. Lavandoside from Lavandula spica flowers. Chem Nat Compd 44, 169–170 (2008).

Additional Infomation
4-O-β-D-glucosyl-trans-ferulic acid is a methoxycinnamic acid derivative of ferulic acid, in which the phenolic hydroxyl group at position 4 is converted to β-D-glucosinolate. It is a plant metabolite. It is a β-D-glucosinolate, monomethoxybenzene, monosaccharide derivative, and methoxycinnamic acid. It is functionally related to ferulic acid. It is the conjugate acid of 4-O-β-D-glucosyl-trans-ferulic acid. (E)-4-hydroxy-3-methoxycinnamic acid 4-O-|AD-glucopyranoside has been reported in tea (Camellia sinensis), potato (Solanum tuberosum), and other organisms with relevant data.
Lavandoside is a research compound not approved for clinical use. It is classified as a natural product with antioxidant and anti-inflammatory potential, making it of interest for studies on oxidative stress, inflammation, and the development of natural antioxidants. No clinical trials have been reported for this compound. The compound is isolated from lavender and Helianthemum ruficomum and has been identified as one of several antioxidant compounds from these sources. It is used for research purposes only and is not intended for therapeutic use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H20O9
Molecular Weight
356.32
Exact Mass
356.11
CAS #
117405-51-3
PubChem CID
13916049
Appearance
White to off-white solid
Density
1.5±0.0 g/cm3
Boiling Point
642.0±0.0 °C at 760 mmHg
Flash Point
235.8±0.0 °C
Vapour Pressure
0.0±0.0 mmHg at 25°C
Index of Refraction
1.650
LogP
-0.79
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
6
Heavy Atom Count
25
Complexity
469
Defined Atom Stereocenter Count
5
SMILES
COC1=CC(\C=C\C(O)=O)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChi Key
IEMIRSXOYFWPFD-BJGSYIFTSA-N
InChi Code
InChI=1S/C16H20O9/c1-23-10-6-8(3-5-12(18)19)2-4-9(10)24-16-15(22)14(21)13(20)11(7-17)25-16/h2-6,11,13-17,20-22H,7H2,1H3,(H,18,19)/b5-3+/t11-,13-,14+,15-,16-/m1/s1
Chemical Name
(E)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
Synonyms
Lavandoside; 2-Propenoic acid, 3-[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]-, (2E)-; (E)-4-Hydroxy-3-methoxycinnamic acid 4-O-; A-D-glucopyranoside; (2E)-3-[4-(beta-D-Glucopyranosyloxy)-3-methoxyphenyl]-2-propenoic acid; (E)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid; Ferulic acid 4-glucoside;
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: 50 mg/mL (140.32 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8065 mL 14.0323 mL 28.0647 mL
5 mM 0.5613 mL 2.8065 mL 5.6129 mL
10 mM 0.2806 mL 1.4032 mL 2.8065 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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