Danshensu

Base Information

• Chemical Name: Danshensu
• CAS No.: 76822-21-4
• Molecular Formula: C₉H₁₀O₅
• Molecular Weight: 198.175
• Hs Code.: 2942000000
• UNII: 4GF33A5PAJ
• ChEMBL ID: CHEMBL4218391
• DSSTox Substance ID: DTXSID60469215
• Nikkaji Number: J418.972H
• Wikidata: Q10395557
• Mol file: 76822-21-4.mol

Synonyms:(3,4-dihydroxyphenyl)lactic acid;3,4-dihydroxyphenyllactic acid;3,4-dihydroxyphenyllactic acid, (+-)-isomer;3,4-dihydroxyphenyllactic acid, (R)-isomer;3,4-dihydroxyphenyllactic acid, monosodium salt;3,4-dihydroxyphenyllactic acid, monosodium salt, (+-)-isomer;3,4-dihydroxyphenyllactic acid, monosodium salt, (R)-isomer;danshensu;salvianic acid A sodium

Chemical Property of Danshensu

Chemical Property:

• Appearance/Colour: ==
• Vapor Pressure: 4.42E-10mmHg at 25°C
• Boiling Point: 481.5 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 259.1 °C
• PSA: 97.99000
• Density: 1.546 g/cm³
• LogP: 0.08580
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Water (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 198.05282342
• Heavy Atom Count: 14
• Complexity: 205

Purity/Quality:

99.8% ^*data from raw suppliers

Danshensu ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1C[C@H](C(=O)O)O)O)O
• Uses: Danshensu increases production of collagenin Detroit 551 cells and attenuates the α-MSH-stimulated melanin production of B16 cells. Danshensu may be used as active ingredients in would healing, cosmetic treatments or treating hyperpigmentation.

Technology Process of Danshensu

There total 52 articles about Danshensu which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate (1339946-92-7) → danshensu (23028-17-3,42085-50-7,69339-96-4,76822-21-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; ethanol; at 20 ℃; for 1.5h;

DOI:10.1016/j.molstruc.2017.09.118

Reference yield: 22.1%

(R)-(+)-rosmarinic acid (20283-92-5) → danshensu (23028-17-3,42085-50-7,69339-96-4,76822-21-4)

Guidance literature:

With methanol; sodium hydroxide; In dichloromethane; at 30 ℃; for 4h;

DOI:10.1080/14756366.2020.1740923

Reference yield:

3-(6-feruloyl-β-D-glucopyranosyl)rosmarinic acid → feruloyl-6-O-β-D-glucopyranoside (137887-25-3) + caffeic acid (331-39-5,501-16-6) + danshensu (23028-17-3,42085-50-7,69339-96-4,76822-21-4)

Guidance literature:

With hydrogenchloride; In water; at 60 ℃; for 3h;

DOI:10.1016/j.phytochem.2014.02.007

upstream raw materials:

(Z)-3-(3,4-dihydroxyphenyl)-2-hydroxyacrylic acid

clinopodic acid C

(R)-(+)-rosmarinic acid

lycopic acid A

Downstream raw materials:

(+/-)-(R)-methyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate

(R)-(+)-rosmarinic acid

(2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid (S)-PGME amide

(2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid (R)-PGME amide

Refernces

• 1、 Olennikov, D. N.. "New Benzofuran Lignans from Nepeta multifida". . p. 818 - 822. Retrieved 2021/09/20.
• 2、 Sidoryk, Katarzyna,Filip, Katarzyna,Cmoch, Piotr,?aszcz, Marta,Cybulski, Marcin. "Efficient synthesis and physicochemical characterization of natural danshensu, its S isomer and intermediates thereof". . p. 135 - 148. Retrieved 2017/10/13.