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Salvianolic acid D

Alias: Salvianolic acid D; 142998-47-8; UNII-28R85321EY; 28R85321EY; (2R)-2-[(E)-3-[2-(carboxymethyl)-3,4-dihydroxyphenyl]prop-2-enoyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid; Benzenepropanoic acid, alpha-(((2E)-3-(2-(carboxymethyl)-3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-3,4-dihydroxy-, (alphaR)-; BENZENEPROPANOIC ACID, .ALPHA.-(((2E)-3-(2-(CARBOXYMETHYL)-3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4-DIHYDROXY-, (.ALPHA.R)-; Salvianolate D;
Cat No.:V14297 Purity: ≥98%
Salvianolic acid D is extracted from Salvia miltiorrhiza and is a compound with potential antiplatelet activity.
Salvianolic acid D
Salvianolic acid D Chemical Structure CAS No.: 142998-47-8
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
Salvianolic acid D is extracted from Salvia miltiorrhiza and is a compound with potential antiplatelet activity.
Biological Activity I Assay Protocols (From Reference)
Targets
Natural product; antiplatelet
ln Vitro
Four water-soluble constituents, salvianolic acids D, E, ethyl lithospermate, and isoferulic acid were isolated from SALVIA MILTIORRHIZA. Salvianolic acids D and E are new depsides. Their chemical structures were determined by chemical and spectral analysis. The structure of Salvianolic acid D was finally confirmed by comparison with a synthetic product. [1]
Platelets play crucial roles in thromboembolic and cardiovascular disease. The main platelets membrane receptors include adenosine diphosphate receptors, thrombin receptors, thromboxane prostanoid receptors and collagen receptors. In this study, a Platelet/CMC coupled with offline UPLC-QTOF-MS/MS system was built to screen antiplatelet activity components from aqueous extract of Danshen, which serve as an agent of antiplatelet aggregation in Traditional Chinese Medicine. Rosmarinic acid, lithospermic acid, salvianolic acid B, two isomers of salvianolic acid B, salvianolic acid C, Salvianolic acid D and salvianolic acid H/I were identified as the potential antiplatelet activity components. Moreover, rosmarinic acid, lithospermic acid, salvianolic acid B, salvianolic acid C and danshensu were tested in platelet aggregation in vitro assay. The results suggested their retention time was closely related to the antiplatelet aggregation activities. This study provides a rapid, effective and novel method for screening the potential antiplatelet activity components from Chinese herb medicines. [2]
Enzyme Assay
Platelet aggregation assay [2]
The platelet was prepared as Section 2.4 and was re-suspended in buffer A and adjusted to a consistent concentration (OD value 1.0). All tested compounds such as Salvianolic acid D were dissolved in DMSO and diluted with buffer A to 50 μM. Buffer A was used as negative control. According to the types of membrane receptors, different agonists were used to induce platelet aggregation. The agonists include thrombin (activator of thrombin receptors), ADP (activator of ADP receptors) and U46619 (activator of TP receptors). The platelet aggregation assay was performed at 37 °C.
100 μL platelet suspension at a concentration of 108 platelet/mL was adopted in the platelet aggregation assay on a transparent 96-well plate. 50 μL samples were added into each wells, meanwhile same amount of buffer A was added in negative control group. 50 μL agonist (0.5 U/mL thrombin, 25 μM ADP or 4 μM U46619) were added into each wells after pre-incubation at 37 °C for 10 min under sustained oscillation. The OD values at 405 nm were recorded every 45 s during 30 min by FlexStation 3 plate reader under sustained oscillation.
References

[1]. Salvianolic Acids D and E: Two New Depsides from Salvia miltiorrhiza. Planta Med. 1992 Apr;58(2):197-9.

[2]. A Platelet/CMC coupled with offline UPLC-QTOF-MS/MS for screening antiplatelet activity components from aqueous extract of Danshen. J Pharm Biomed Anal. 2016 Jan 5;117:178-83.

Additional Infomation
Salvianolic acid D is a hydroxycinnamic acid.
Salvianolic acid D has been reported in Salvia miltiorrhiza and Salvia chinensis with data available.
In summary, a Platelet/CMC coupled with offline UPLC-QTOF-MS/MS system was built successfully to screen antiplatelet activity components from aqueous extract of Danshen. RA, LA, SAB, two isomers of SAB, SAC, SAD/Salvianolic acid D and SAH/I were identified as the potential antiplatelet activity components. The results of platelet aggregation assay suggested retention time of 5 compounds (DSS, RA, LA, SAB and SAC) was closely related to the antiplatelet aggregation activities. It is believed that the developed Platelet/CMC offline UPLC-QTOF-MS/MS system is novel and viable strategy for screening the potential antiplatelet activity components from TCMs and herbal medicine.[2]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H18O10
Molecular Weight
418.3509
Exact Mass
418.089
Elemental Analysis
C, 57.42; H, 4.34; O, 38.24
CAS #
142998-47-8
PubChem CID
75412558
Appearance
Light yellow to yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
786.9±60.0 °C at 760 mmHg
Flash Point
280.2±26.4 °C
Vapour Pressure
0.0±2.9 mmHg at 25°C
Index of Refraction
1.717
LogP
0.98
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
9
Heavy Atom Count
30
Complexity
648
Defined Atom Stereocenter Count
1
SMILES
C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C(C(=C(C=C2)O)O)CC(=O)O)O)O
InChi Key
KFCMFABBVSIHTB-WUTVXBCWSA-N
InChi Code
InChI=1S/C20H18O10/c21-13-4-1-10(7-15(13)23)8-16(20(28)29)30-18(26)6-3-11-2-5-14(22)19(27)12(11)9-17(24)25/h1-7,16,21-23,27H,8-9H2,(H,24,25)(H,28,29)/b6-3+/t16-/m1/s1
Chemical Name
(2R)-2-[(E)-3-[2-(carboxymethyl)-3,4-dihydroxyphenyl]prop-2-enoyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid
Synonyms
Salvianolic acid D; 142998-47-8; UNII-28R85321EY; 28R85321EY; (2R)-2-[(E)-3-[2-(carboxymethyl)-3,4-dihydroxyphenyl]prop-2-enoyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid; Benzenepropanoic acid, alpha-(((2E)-3-(2-(carboxymethyl)-3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-3,4-dihydroxy-, (alphaR)-; BENZENEPROPANOIC ACID, .ALPHA.-(((2E)-3-(2-(CARBOXYMETHYL)-3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4-DIHYDROXY-, (.ALPHA.R)-; Salvianolate D;
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 2.3903 mL 11.9517 mL 23.9034 mL
5 mM 0.4781 mL 2.3903 mL 4.7807 mL
10 mM 0.2390 mL 1.1952 mL 2.3903 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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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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