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Lupulone

CAT: 0804-HY-124923-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-124923-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Lupulone is a beta-acid from the hop plant H. lupulus with diverse biological activities including antibacterial, antioxidant, and anticarcinogenic properties[1][2][3].
CAS Number
468-28-0
UNSPSC
12352211
Hazard Statement
H302, H315, H319, H335
Target
Bacterial
Type
Natural Products
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/lupulone.html
Purity
99.0
Solubility
DMSO : 40 mg/mL (ultrasonic; warming)
Smiles
O=C1C(C/C=C(C)\C)=C(C(C(CC(C)C)=O)=C(C1(C/C=C(C)\C)C/C=C(C)\C)O)O
Molecular Formula
C26H38O4
Molecular Weight
414.58
Precautions
H302, H315, H319, H335
References & Citations
[1]Tagashira M, et al. Antioxidative activity of hop bitter acids and their analogues. Biosci Biotechnol Biochem. 1995 Apr;59 (4) :740-2. |[2]Lamy V, et al. Lupulone, a hop bitter acid, activates different death pathways involving apoptotic TRAIL-receptors, in human colon tumor cells and in their derived metastatic cells. Apoptosis 13 (10), 1232-1242 (2008) .|[3]Bocquet L, et al. Phenolic Compounds from Humulus lupulus as Natural Antimicrobial Products: New Weapons in the Fight against Methicillin Resistant Staphylococcus aureus, Leishmania mexicana and Trypanosoma brucei Strains. Molecules. 2019 Mar 14;24 (6) :1024.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Lupulone

Lupulone is a beta-bitter acid in which the acyl group is specified as 3-methylbutanoyl. It has a role as an antimicrobial agent, an antineoplastic agent, an angiogenesis inhibitor and an apoptosis inducer. It is a conjugate acid of a lupulone(1-).

CAS Number468-28-0
PubChem CID68051
IUPAC Name3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
Molecular FormulaC26H38O4
Molecular Weight414.6
XLogP6.7
Topological Polar Surface Area74.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Heavy Atom Count30
Formal Charge0
Complexity812
SMILES
CC(C)CC(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)CC=C(C)C)O)CC=C(C)C)O
InChI
InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28-29H,10,13-15H2,1-8H3
InChIKey
LSDULPZJLTZEFD-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Lupulone
CAS: 468-28-0
CID: 68051
Formula: C26H38O4
MW: 414.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight414.6
XLogP36.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Exact Mass414.27700969
Monoisotopic Mass414.27700969
Topological Polar Surface Area74.6 Ų
Heavy Atom Count30
Formal Charge0
Complexity812
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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