Strictosidine

Base Information

• Chemical Name: Strictosidine
• CAS No.: 20824-29-7
• Molecular Formula: C₂₇H₃₄N₂O₉
• Molecular Weight: 530.575
• UNII: 45T874R5N4
• DSSTox Substance ID: DTXSID40943068
• Nikkaji Number: J15.956E
• Wikipedia: Strictosidine
• Wikidata: Q2356148
• Metabolomics Workbench ID: 50958
• ChEMBL ID: CHEMBL402211
• Mol file: 20824-29-7.mol

Synonyms:isovincoside;strictosidine;strictosidine, (2S-(2alpha,3beta,4beta(S*)))-isomer

Chemical Property of Strictosidine

Chemical Property:

• Vapor Pressure: 1.78E-24mmHg at 25°C
• Melting Point: 161-165 °C
• Boiling Point: 763°Cat760mmHg
• PKA: 12.81±0.70(Predicted)
• Flash Point: 415.3°C
• PSA: 162.73000
• Density: 1.44g/cm³
• LogP: 0.72170
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 530.22643067
• Heavy Atom Count: 38
• Complexity: 887

Purity/Quality:

98%Min ^*data from raw suppliers

Strictosidine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=COC(C(C1CC2C3=C(CCN2)C4=CC=CC=C4N3)C=C)OC5C(C(C(C(O5)CO)O)O)O
• Isomeric SMILES: COC(=O)C1=CO[C@H]([C@@H]([C@@H]1C[C@H]2C3=C(CCN2)C4=CC=CC=C4N3)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• Description: A glycoalkaloid occurring in Vinca rosea, this base is probably stereoisomeric with Vincoside and Strictosidine (q.v.), the latter two alkaloids almost certainly being identical. It is a pale yellow amorphous solid, yielding the N:N' -diacetyl derivative, m.p. 171°C and an amorphous pentaacetyl compound which is laevorotatory with [α] D - 75° (CHCI3).
• Uses: Strictosidine is studied as a potential antimalarial compound.

Technology Process of Strictosidine

There total 25 articles about Strictosidine 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: 84.0%

tryptamine (61-54-1) + secologanin (19351-63-4) → strictosidine (19456-89-4,20824-29-7)

Guidance literature:

In aq. phosphate buffer; at 5 ℃; Enzymatic reaction;

Reference yield: 35.2%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 5-carboxystrictosidine → strictosidine (19456-89-4,20824-29-7) + dolichantoside (68727-52-6)

Guidance literature:

DOI:10.1248/cpb.45.1231

Reference yield: 27.0%

secologanin (19351-63-4) + tryptamine hydochloride (343-94-2) → strictosamide (22621-94-9,23141-27-7,23141-25-5) + strictosidine (19456-89-4,20824-29-7) + 3β(R)-vincosamide (23141-27-7,22621-94-9,23141-25-5)

Guidance literature:

With tryptamine; acetic acid; In water; at 100 ℃; for 6h;

DOI:10.1021/np990150r

upstream raw materials:

tryptamine

secologanin

(4S)-6t-[tetrakis-O-(2,2,2-trichloro-ethoxycarbonyl)-β-D-glucopyranosyloxy]-4r-[(S)-2-(2,2,2-trichloro-ethoxycarbonyl)-2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl]-5c-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

diazomethane

Downstream raw materials:

16(R),19(Z)-isositsirikine

16R-E-isositsirikine

strictosidine aglycone

tetrahydroalstonine

Refernces

• 1、 Ishikawa, Hayato,Rakumitsu, Kenta,Sakamoto, Jukiya,Sumimoto, Michinori,Umeda, Yuhei. "Total Syntheses of (?)-Strictosidine and Related Indole Alkaloid Glycosides". . p. 13414 - 13422. Retrieved 2020/06/08.
• 2、 Cai, Yunrui,Zhu, Huajian,Alperstein, Zaccary,Yu, Wenjun,Cherkasov, Artem,Zou, Hongbin. "Strictosidine Synthase Triggered Enantioselective Synthesis of N-Substituted (S)-3,14,18,19-Tetrahydroangustines as Novel Topoisomerase i Inhibitors". . p. 3086 - 3092. Retrieved 2017/12/26.