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Cinnamtannin D2

Cat No.:V61677 Purity: ≥98%
Cinnamtannin D2 (compound 13) is a cinnamon tannin extracted from Vaccinium vitis-idaea L.
Cinnamtannin D2
Cinnamtannin D2 Chemical Structure CAS No.: 97233-47-1
Product category: Phenols
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
Cinnamtannin D2 (compound 13) is a cinnamon tannin extracted from Vaccinium vitis-idaea L.
Cinnamtannin D2 (CAS#: 97233-47-1) is a naturally occurring A-type proanthocyanidin (a cinnamon tannin) isolated from Vaccinium vitis-idaea L. (lingonberry) and other plant sources including Cinnamomum sieboldii. It is a complex polyphenolic compound with a molecular formula C60H48O24 and molecular weight of approximately 1153 Da. As a member of the A-type procyanidin family, it consists of multiple flavan-3-ol units (catechin/epicatechin) linked via C4→C8 and C2→O→C7 bonds. This compound is of research interest for its antioxidant and potential anti-inflammatory properties.
Biological Activity I Assay Protocols (From Reference)
Targets
Cinnamtannin D2 is a naturally occurring polyphenol that does not target a single specific receptor or enzyme. Instead, its biological activities are mediated through multiple mechanisms typical of A-type proanthocyanidins. These include free radical scavenging (antioxidant activity), inhibition of polyphenol oxidase, modulation of cellular redox status, and potential interaction with proteins involved in inflammatory signaling pathways. Some A-type procyanidins have also been reported to inhibit hepatitis C virus (HCV) entry into human hepatocytes in a dose-dependent manner.
ln Vitro
In vitro, A-type procyanidins (including compounds structurally related to Cinnamtannin D2) exhibit antioxidant activity through free radical scavenging and inhibition of polyphenol oxidase. They significantly and dose-dependently inhibit hepatitis C virus (HCV) entry into human hepatocytes. The compound has been isolated from Vaccinium vitis-idaea L. and is used in natural product research to study the biological activities of A-type proanthocyanidins. Specific quantitative activity data for Cinnamtannin D2 itself are limited; most information is extrapolated from studies on related A-type procyanidins.
ln Vivo
In vivo studies for Cinnamtannin D2 are limited. Based on the known activities of A-type proanthocyanidins, this compound would be expected to exhibit systemic antioxidant effects following oral absorption, although the bioavailability of high-molecular-weight polyphenols is generally low. Most ingested proanthocyanidins are metabolized by gut microbiota to smaller phenolic acids that may mediate some of the observed health benefits. No specific in vivo efficacy studies for Cinnamtannin D2 have been reported in the literature.
Enzyme Assay
Cell-free antioxidant assay protocol (DPPH radical scavenging): Varying concentrations of Cinnamtannin D2 (1-200 microM) are mixed with DPPH (2,2-diphenyl-1-picrylhydrazyl) radical solution in methanol or ethanol. The mixture is incubated at room temperature for 30 minutes in the dark. Absorbance is measured at 517 nm, and the percentage of radical scavenging is calculated relative to a control without compound. IC50 values are determined from dose-response curves. Trolox or ascorbic acid is typically used as a positive control.
Cell Assay
Cell-based antioxidant activity: Cultured cells (e.g., HepG2 hepatocytes or primary neurons) are pretreated with Cinnamtannin D2 (1-50 microM) for 2-24 hours, then exposed to an oxidative stressor such as hydrogen peroxide (100-500 microM). Cell viability is assessed by MTT assay, and markers of oxidative stress (e.g., reactive oxygen species measured by DCFH-DA fluorescence, malondialdehyde levels, glutathione depletion) are quantified. Alternatively, the compound can be tested for its ability to inhibit HCV entry using human hepatoma cell lines.
Animal Protocol
In vivo animal studies for Cinnamtannin D2 have not been reported in the literature. For related proanthocyanidins, typical protocols involve oral administration to rodents (e.g., 50-200 mg/kg/day) for assessment of antioxidant, anti-inflammatory, or hepatoprotective effects. Pharmacodynamic endpoints include measurement of serum markers of oxidative stress and inflammation, liver enzyme levels (ALT, AST), and histological analysis of tissue sections. However, these studies have not been conducted specifically with isolated Cinnamtannin D2.
ADME/Pharmacokinetics
Pharmacokinetic data for Cinnamtannin D2 are not available. As a high-molecular-weight polyphenol (1153 Da) with extensive hydrogen bonding capacity, its oral bioavailability is expected to be low (typically <1-5% for similar proanthocyanidins). The compound likely undergoes extensive metabolism by gut microbiota to smaller phenolic acids (e.g., 3-hydroxyphenylpropionic acid, 3-hydroxybenzoic acid, and hippuric acid), which are absorbed and undergo further phase II conjugation (glucuronidation, sulfation) before urinary excretion. The parent compound may not reach systemic circulation in significant amounts.
Toxicity/Toxicokinetics
Toxicity studies for Cinnamtannin D2 have not been performed. As a naturally occurring A-type procyanidin found in edible plants such as lingonberries and cinnamon, the compound is generally considered safe at concentrations present in the diet. High doses of proanthocyanidin-rich extracts have been used in animal studies without significant toxicity. However, isolated Cinnamtannin D2 is a research chemical, and its toxicological profile has not been formally evaluated. Standard laboratory safety precautions for handling natural products should be followed.
References

[1]. Tannins and Related Compounds. LX.: Isolation and Characterization of Proanthocyanidins with a Doubly-Linked Unit from Vaccinium vitis-idaea L. Chemical and pharmaceutical bulletin, 1988, 36(1): 33-38.

Additional Infomation
Cinnamtannin D2 is a proanthocyanidin. It has been reported that cinnamtannin D2 exists in the genus *Cinnamomum* sieboldii and *Cinnamomum burmanni*, and relevant data are available for reference.
Cinnamtannin D2 is not a drug and has no clinical applications or regulatory approval for therapeutic use. It is a naturally occurring A-type proanthocyanidin (cinnamon tannin) isolated from Vaccinium vitis-idaea L. (lingonberry). It is used in natural product chemistry research, phytochemical analysis, and studies of proanthocyanidin structure-activity relationships. The compound belongs to the class of biflavonoids and polyflavonoids and has been detected in fruits and lingonberries. It is supplied as a purified solid for research use only. Not for human consumption.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C60H48O24
Molecular Weight
1153.00873947144
Exact Mass
1152.253
CAS #
97233-47-1
PubChem CID
168006196
Appearance
Typically exists as solid at room temperature
LogP
4.3
Hydrogen Bond Donor Count
19
Hydrogen Bond Acceptor Count
24
Rotatable Bond Count
6
Heavy Atom Count
84
Complexity
2280
Defined Atom Stereocenter Count
10
SMILES
C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@@H]3[C@H]([C@H](OC4=C3C(=CC5=C4[C@@H]6C([C@](O5)(OC7=C(C(=CC(=C67)O)O)[C@@H]8[C@H]([C@H](OC9=CC(=CC(=C89)O)O)C1=CC(=C(C=C1)O)O)O)C1=CC(=C(C=C1)O)O)O)O)C1=CC(=C(C=C1)O)O)O)O)O)C1=CC(=C(C=C1)O)O)O
InChi Key
QRQAODSINXAOBF-BITWWPEZSA-N
InChi Code
InChI=1S/C60H48O24/c61-23-13-34(71)42-40(14-23)80-54(20-2-6-26(63)31(68)10-20)51(77)48(42)45-36(73)17-37(74)46-50-47-41(83-60(59(50)79,84-58(45)46)22-4-8-28(65)33(70)12-22)18-38(75)44-49(52(78)55(82-57(44)47)21-3-7-27(64)32(69)11-21)43-35(72)16-29(66)24-15-39(76)53(81-56(24)43)19-1-5-25(62)30(67)9-19/h1-14,16-18,39,48-55,59,61-79H,15H2/t39-,48+,49-,50+,51+,52+,53+,54+,55+,59+,60+/m0/s1
Chemical Name
(1R,5R,6R,7S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
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

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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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 0.8673 mL 4.3365 mL 8.6730 mL
5 mM 0.1735 mL 0.8673 mL 1.7346 mL
10 mM 0.0867 mL 0.4336 mL 0.8673 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 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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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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g/mol

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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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