Secologanin

Base Information Edit

Chemical Name:Secologanin
CAS No.:19351-63-4
Molecular Formula:C17H24 O10
Molecular Weight:388.372
Hs Code.:
UNII:NK7B26K93T
DSSTox Substance ID:DTXSID30941033
Nikkaji Number:J15.538A
Wikipedia:Secologanin
Wikidata:Q1531155
Metabolomics Workbench ID:28055
ChEMBL ID:CHEMBL1235867
Mol file:19351-63-4.mol

Synonyms:secologanin

Suppliers and Price of Secologanin

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Sigma-Aldrich
Secologanin analytical standard
5 mg
$ 86.60

Sigma-Aldrich
Secologanin analytical standard
5mg-f
$ 83.90

ChemScene
Secologanin
5mg
$ 250.00

Cayman Chemical
Secologanin ≥90%
1mg
$ 25.00

Cayman Chemical
Secologanin ≥90%
5mg
$ 69.00

Biosynth Carbosynth
(-)-Secologanin
2 mg
$ 70.00

Biosynth Carbosynth
(-)-Secologanin
1 mg
$ 50.00

Biosynth Carbosynth
(-)-Secologanin
5 mg
$ 100.00

AHH
Secologanin 90%
0.05g
$ 296.00

Total 13 raw suppliers

Chemical Property of Secologanin Edit

Chemical Property:

Vapor Pressure:1.15E-16mmHg at 25°C
Boiling Point:595.5°Cat760mmHg
PKA:12.81±0.70(Predicted)
Flash Point:212.2°C
PSA：151.98000
Density:1.42g/cm³
LogP:0.20990
Storage Temp.:−20°C
XLogP3:-1.6
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:8
Exact Mass:388.13694696
Heavy Atom Count:27
Complexity:576

Purity/Quality:

98%,99%, ^*data from raw suppliers

Secologanin analytical standard ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: Total 1 MSDS from other Authors

Useful:

Canonical SMILES:COC(=O)C1=COC(C(C1CC=O)C=C)OC2C(C(C(C(O2)CO)O)O)O
Isomeric SMILES:COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC=O)C=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Description Secologanin is a monoterpene that has been found in V. rosea and is an intermediate in the synthesis of monoterpene indole alkaloids from geraniol. It is a metabolite of loganin formed by the cytochrome P450 (CYP) isoform CYP72A1, also known as secologanin synthase.
Uses (-?)?-?Secologanin is an iridoid glycoside found in Hydrangeaceae used in anti-inflammatory.

Technology Process of Secologanin

There total 11 articles about Secologanin 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: 94.0%

: 27856-66-2
O,O,O,O-tetraacetylsecologaninn

: 19351-63-4
secologanin

Guidance literature:: O,O,O,O-tetraacetylsecologaninn; In methanol; at 20 ℃; for 0.5h;

With potassium carbonate; In methanol; at 0 ℃; for 0.166667h;

In water; acetone; at 20 ℃; for 5h;
DOI:10.1002/chem.201902073

Reference yield: 81.0%

: 18524-94-2
loganin

: 19351-63-4
secologanin

Guidance literature:: With IR 120 (H+); water; In acetonitrile; at 5 ℃; for 144h;

Reference yield:

: C₂₄H₃₂O₁₃

: 19351-63-4
secologanin

Guidance literature:: Multi-step reaction with 4 steps

1.1: tributylphosphine; ortho-nitrophenyl selenocyanate / tetrahydrofuran / 0.33 h / 23 °C / Inert atmosphere

1.2: 16 h / 0 - 23 °C / Inert atmosphere

2.1: t-butyldimethylsiyl triflate; triethylamine / tetrahydrofuran / 0.18 h / -78 - 23 °C / Inert atmosphere

2.2: 0.53 h / -78 - 23 °C / Inert atmosphere

3.1: lead(IV) tetraacetate / 1.5 h / -20 °C / Inert atmosphere

4.1: lithium methanolate / methanol / 5 h / 0 °C / Inert atmosphere

With ortho-nitrophenyl selenocyanate; tributylphosphine; t-butyldimethylsiyl triflate; lithium methanolate; lead(IV) tetraacetate; triethylamine; In tetrahydrofuran; methanol;
DOI:10.1021/jacs.1c02004