ChemicalBook > CAS DataBase List > Micheliolide

Micheliolide

Product Name
Micheliolide
CAS No.
68370-47-8
Chemical Name
Micheliolide
Synonyms
CS-1321;Mecheliolide;Micheliolide;Micheliolide, BR;Micheliolide 68370-47-8;Micheliolide, 10 mM in DMSO;Nuclear factor-κB,NF-κB,inhibit,Micheliolide,Nuclear factor-kappaB,Inhibitor;(3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one;(3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one;(3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
CBNumber
CB42339810
Molecular Formula
C15H20O3
Formula Weight
248.32
MOL File
68370-47-8.mol
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Micheliolide Property

Melting point:
131-133 °C
Boiling point:
426.1±45.0 °C(Predicted)
Density 
1.17±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Solid
pka
14.65±0.40(Predicted)
color 
Off-White
InChI
InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/m0/s1
InChIKey
RDJAFOWISVMOJY-PWNZVWSESA-N
SMILES
O1C(=O)C(=C)[C@]2([H])CCC(C)=C3[C@@]([H])([C@@]12[H])[C@@](O)(C)CC3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC
Product number
M342365
Product name
Micheliolide
Packaging
100mg
Price
$475
Updated
2021/12/16
Usbiological
Product number
361826
Product name
Micheliolide
Packaging
20mg
Price
$523
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
66282
Product name
Micheliolide
Packaging
100mg
Price
$975
Updated
2021/12/16
Arctom
Product number
AS019584
Product name
Micheliolide
Purity
≥98%
Packaging
1mg
Price
$114
Updated
2021/12/16
Arctom
Product number
SY232781
Product name
Micheliolide
Purity
≥98%
Packaging
10mg
Price
$190.91
Updated
2021/12/16
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Micheliolide Chemical Properties,Usage,Production

Uses

Micheliolide, a sesquiterpene lactone is used in the inhibition of resistant acute leukemic cells. Selectively targets cancer stem and progenitor cells.

Definition

ChEBI: Micheliolide is a sesquiterpene lactone.

Biological Activity

Micheliolide (MCL) is a sesquiterpene lactone isolated from Michelia compressa and Michelia champaca. Previous studies have demonstrated that MCL exerted various therapeutic effects in cancer, inflammation, immunomodulatory acute myelogenous leukemia and renal fibrosis through numerous signaling pathways, including PI3K/Akt, NF-kB and MAPK signaling. Dimethylaminomicheliolide (DMAMCL), the prodrug of MCL, has been approved by the US Food and Drug Administration for its apparent efficacy in treating pleomorphic glioblastoma. In China, DMAMCL is currently undergoing clinical trials to treat several advanced or metastatic solid carcinomas, including gliomas[2].

Source

Micheliolide (MCL) is a potentially stable sesquiterpene lactone, which can be isolated from Magnolia grandiflora L., Michelia champaca L., and Michelia compressa (Maxim.) Sarg. MCL and its Michael adduct dimethylaminomicheliolide (DMAMCL) display significant cytotoxicity against tumours. MCL is known to be firstly isolated by Ogura, Cordell from Michelia compressa (Maxim.) Sarg. as a cytotoxic active component. MCL is also a main biologically active constituent of Michelia champaca L., Magnolia grandiflora L., and Tanacetum parthenium Sch. Bip., Anthemis scrobicularis Yavin, and Michelia compressa (Maxim.) Sarg[1].
  

References

[1] Jalal Uddin. “Pharmacological potential of micheliolide: A focus on anti-inflammatory and anticancer activities.” Heliyon 10 6 (2024): e27299.
[2] Dingkun Feng. “Micheliolide suppresses the viability, migration and invasion of U251MG cells via the NF-κB signaling pathway.” Oncology Letters 20 4 (2020): 67.

Micheliolide Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Micheliolide manufacturers

NanJing Spring & Autumn Biological Engineering CO., LTD.
Product
Micheliolide 68370-47-8 68370-47-8
Price
US $75.00/mg
Min. Order
20mg
Purity
≥98%
Supply Ability
1000.00 kgs
Release date
2019-07-09
Career Henan Chemical Co
Product
3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one 68370-47-8
Price
US $1.00/KG
Min. Order
1KG
Purity
85.0-99.8%
Supply Ability
200kgs
Release date
2020-01-10

68370-47-8, MicheliolideRelated Search:


  • (3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one
  • Micheliolide
  • [3aS-(3aalpha,9alpha,9aalpha,9bbeta)]-3a,4,5,7,8,9,9a,9b-Octahydro-9-hydroxy-6,9-dimethyl-3-methylene-azuleno[4,5-b]furan-2(3H)-one
  • Micheliolide, BR
  • CS-1321
  • Micheliolide 68370-47-8
  • Mecheliolide
  • Azuleno[4,5-b]furan-2(3H)-one, 3a,4,5,7,8,9,9a,9b-octahydro-9-hydroxy-6,9-dimethyl-3-methylene-, (3aS,9R,9aS,9bS)-
  • (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
  • (3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one
  • Nuclear factor-κB,NF-κB,inhibit,Micheliolide,Nuclear factor-kappaB,Inhibitor
  • Micheliolide, 10 mM in DMSO
  • 68370-47-8