Lupulone
Basic information
- CAS
468-28-0- Standard SMILES
CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(=O)CC(C)C)=C1O- InChIKey
LSDULPZJLTZEFD-UHFFFAOYSA-N- Molecular formula
- C26H38O4
- Average molar mass
- 414.6 g/mol
- Monoisotopic mass
- 414.27700969
Overview
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-).
Names & identifiers
- Preferred name
- Lupulone
- IUPAC
- 3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
- English name
- LUPULONE
- Molecular formula
- C26H38O4
- Molecular weight
- 414.58
Names & synonyms
Lupulone468-28-0beta-Lupulic acid3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-oneCHEBI:6574RefChem:1088600Lupulonbeta-Bitter acidB'' -AcidLupolonEINECS 207-405-3.beta.-Bitter acid
Show more names
b’’-acidB-LUPULIC ACIDlohexadien-1-oneLupulone beta-acidCoclaurine Impurity 3Lupulone (stable DCHA salt)
.beta.-Lupulic acid3,5-Dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one2,4-Cyclohexadien-1-one, 3,5-dihydroxy-4-isovaleryl-2,6,6-tris(3-methyl-2-butenyl)-B7425USG943,5-Dihydroxy-2,6,6-tris(3-methylbuten-2-yl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one2,4-Cyclohexadien-1-one,3,5-dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-n-lupuloneUNII-B7425USG94
Database identifiers
- CAS
468-28-0- PubChem CID
- 68051
Properties
Computed structural properties
- XLogP
- 6.7
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 812
Physicochemical properties
- Melting point
- 93 ℃ · 93℃
- Boiling point
- 453.43 °C · 453.43°C (rough estimate)
- Density
- 1.045 · 1.045±0.06 g/cm3 (20 ºC 760 Torr)
- vapor pressure
- 0 Pa · 0Pa at 20℃
- refractive index
- 1.484 · 1.4840 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Methanol: slightly soluble
- form
- A solid
- pka
- 4.5 · 4.50±1.00(Predicted)
- color
- White to off-white
- Water Solubility
- 1 g/L · 1g/L at 20℃
- Stability
- Hygroscopic
- Major Application
- food and beveragespharmaceutical
- LogP
- 4.5 at · 4.5 at 20℃
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7425 USG94 · B7425USG94
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (90.5%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationREACH registered substance: 3,5-dihydroxy-2,6,6-tris(3-methylbuten-2-yl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one (EC: 207-405-3)
Hazard Classes and CategoriesAcute Tox. 3 (90.5%)
Safety data
- wgk
- WGK 3
- rtecs
- OK5950000
- ridadr
- 2811
- Toxicity
- LD50 in mice, rats (mg/kg): 525, 100 orally (Hnsel, Wagener)
- risk_code
- 25
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- T
- safety_code
- 45
- hazard_class
- 6.1(b)
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
- H315-H312-H302-H319-H317
- REACH Registrations
- Active
Chemistry & industry
Applications
UsesLupulone is a hop plant (Humulus lupulus L.) acid that inhibits tumorigenicity of hepatocellular carcinoma cells.
Additional notes
DefinitionChEBI: 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 apoptosis inducer, an angiogenesis inhibitor and an antineoplastic agent. It is a conjugate acid of a lupulone(1-).
Related reactions
0 records
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Compound notes
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