Gilvocarcin M

Base Information

Chemical Name:Gilvocarcin M
CAS No.:77879-89-1
Molecular Formula:C₂₆H₂₆O₉
Molecular Weight:482.487
Hs Code.:
Nikkaji Number:J440.905A
Wikidata:Q104949200
Metabolomics Workbench ID:161510
ChEMBL ID:CHEMBL5206779
Mol file:77879-89-1.mol

Synonyms:4-fucofuranosyl 1-hydroxy-10,12-dimethoxy-8-vinyl-6H-benz(d)naphtho(1,2b)pyran-6-one 8-methyl ester;gilvocarcin M

Suppliers and Price of Gilvocarcin M

Supply Marketing:

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

Usbiological
Gilvocarcin M
500ug
$ 523.00

TRC
GilvocarcinM
500μg
$ 295.00

Cayman Chemical
Gilvocarcin M ≥95%
2.5mg
$ 931.00

Cayman Chemical
Gilvocarcin M ≥95%
500μg
$ 287.00

American Custom Chemicals Corporation
GILVOCARCIN M 95.00%
5MG
$ 495.11

AK Scientific
1-Hydroxy-10,12-dimethoxy-8-methyl-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]naphtho[1,2-c]isochromen-6-one
2.5mg
$ 1262.00

Total 6 raw suppliers

Chemical Property of Gilvocarcin M

Chemical Property:

Vapor Pressure:1.26E-26mmHg at 25°C
Boiling Point:794.6°C at 760 mmHg
Flash Point:272.5°C
PSA：138.82000
Density:1.446g/cm³
LogP:2.67310
XLogP3:2.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:4
Exact Mass:482.15768240
Heavy Atom Count:35
Complexity:778

Purity/Quality:

98%Min ^*data from raw suppliers

Gilvocarcin M ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1=CC2=C(C(=C1)OC)C3=C(C4=C(C=CC(=C4C(=C3)OC)O)C5C(C(C(O5)C(C)O)O)O)OC2=O
Isomeric SMILES:CC1=CC2=C(C(=C1)OC)C3=C(C4=C(C=CC(=C4C(=C3)OC)O)[C@@H]5[C@@H]([C@H]([C@@H](O5)[C@@H](C)O)O)O)OC2=O
Description Gilvocarcin M is an antibiotic originally isolated from S. gilvotanareus. It is active against S. aureus when used at a concentration of 32 μg/ml. Gilvocarcin M inhibits growth of KB cells (IC50 = 0.52 μg/ml) but has no effect on survival in a P388 mouse model of leukemia when used at doses ranging from 25 to 400 mg/kg. Gilvocarcin M intercalates into bacteriophage PM2 DNA. It is toxic to rats with an intravenous LD50 value of 450 mg/kg.
Uses Gilvocarcin M is the minor analogue of a complex of C-glycoside antitumour actives isolated from a Streptomyces sp.. Gilvocarcin M contains a methyl group in the 8-position, and is less active than the vinyl analogue (gilvocarcin V), which is thought to act as an inhibitor of human topoisomerase II. Gilvocarcin M displays potent antibacterial, antifungal, antiviral and antitumour activity. Recent research suggests that the gilvocarcins act as photoactivated crosslinkers of DNA to histones. Gilvocarcin M is the minor analogue of a complex of C-glycoside antitumor actives isolated from a Streptomyces sp.. Gilvocarcin M contains a methyl group in the 8-position, and is less active than the vinyl analogue (gilvocarcin V), which is thought to act as an inhibitor of human topoisomerase II. Gilvocarcin M displays potent antibacterial, antifungal, antiviral and antitumor activity. Recent research suggests that the gilvocarcins act as photoactivated cross-linkers of DNA to histones. Gilvocarcin M is the minor analogue of Gilvocarcin V with anti-bact, -fungal, -viral and -tumor activity.

Technology Process of Gilvocarcin M

There total 10 articles about Gilvocarcin M 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: 89.5%

: 155351-67-0
1-(benzyloxy)-10,12-dimethoxy-8-methyl-4-(2,3,5-tri-O-benzyl-α-D-fucofuranosyl)-6H-benzonaphtho<1,2-b>pyran-6-one

: 77879-89-1
gilvocarcin M

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 5h; under 760 Torr; Ambient temperature;
DOI:10.1021/ja00082a023

Reference yield: 72.0%

: 140201-81-6
1-Benzyloxy-4-[(2S,3R,4S,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yl]-10,12-dimethoxy-8-methyl-dibenzo[c,h]chromen-6-one

: 140459-76-3,77879-89-1
(+)-gilvocarcin M

Guidance literature:: With hydrogen; nickel; In ethanol; for 72h; under 760 Torr; Ambient temperature;
DOI:10.1021/ja00035a069

Reference yield:

: 133344-02-2
2-iodo-3-methoxy-5-methylbenzoic acid

: 77879-89-1
gilvocarcin M

Guidance literature:: Multi-step reaction with 4 steps

1: (COCl)2, DMF / CH₂Cl₂ / 1 h / Ambient temperature

2: 91.3 percent / i-Pr₂NEt, DMAP / tetrahydrofuran / 2 h / Ambient temperature

3: 89.3 percent / (Ph₃P)2PdCl₂, NaOAc / N,N-dimethyl-acetamide / 5 h / 125 °C

4: 89.5 percent / H₂ / 10percent Pd/C / methanol / 5 h / 760 Torr / Ambient temperature

With dmap; bis-triphenylphosphine-palladium(II) chloride; oxalyl dichloride; hydrogen; sodium acetate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide;
DOI:10.1021/ja00082a023