Marrubiin
Basic information
- CAS
465-92-9- Standard SMILES
C[C@@H]1C[C@H]2OC(=O)[C@@]3(C)CCC[C@@](C)([C@@H]23)[C@@]1(O)CCc1ccoc1- InChIKey
HQLLRHCTVDVUJB-OBHOOXMTSA-N- Molecular formula
- C20H28O4
- Average molar mass
- 332.4 g/mol
- Monoisotopic mass
- 332.19875937
Overview
Marrubiin is a gamma-lactone.
Names & identifiers
- Preferred name
- Marrubiin
- IUPAC
- (1R,4S,8S,9R,10R,12R)-9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one
- English name
- MARRUBIIN
- Molecular formula
- C20H28O4
- Molecular weight
- 332.43
Names & synonyms
Marrubiin465-92-9DTXSID50963595AP086P88M4NSC-36693(1R,4S,8S,9R,10R,12R)-9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one(1R,4S,8S,9R,10R,12R)-9-(2-(furan-3-yl)ethyl)-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo(6.3.1.04,12)dodecan-3-oneRefChem:810635DTXCID501764789MFCD08461003MARRUBINNSC36693
Show more names
MARRUBIIN(P)MARRUBIIN(SH)MarrubiuM bitterMARRUBIIN(AS) 10mg5-[2-(3-furyl)ethyl]decahydro-5-hydroxy-1,4a,6-trimethyl-1,8-naphthalenecarbolactone6β-[2-(3-Furanyl)ethyl]decahydro-6α-hydroxy-2aα,5aβ,7α-trimethyl-2H-naphtho[1,8-bc]furan-2-one2H-Naphtho[1,8-bc]furan-2-one, 6-[2-(3-furanyl)ethyl]decahydro-6-hydroxy-2a,5a,7-trimethyl-, (2aS,5aS,6R,7R,8aR,8bR)-
MLS000738128UNII-AP086P88M4Marrubiin CRSNSC 36693Marrubiin (Standard)MARRUBIIN [MI]Marrubiin (Marrubium bitter).CHEBI:6696
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 59.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 534
Physicochemical properties
- Melting point
- 159 · 159-162°C
- alpha
- 20 · D20 +35.8° (c = 3.1 in chloroform); D24 +45° (acetone)
- Boiling point
- 297 · 297-299 °C(Press: 15 Torr)
- Density
- 1.152 · 1.152±0.06 g/cm3 (20 ºC 760 Torr)
- storage temp.
- 4 °C, · 4°C, protect from light
- solubility
- 100 mg/mL · DMSO: 100 mg/mL (300.82 mM)
- form
- A solid
- pka
- 14.66 · 14.66±0.70(Predicted)
- color
- White to off-white
- biological source
- plant
- optical activity
- 35.82 · +35.820 (c 3.1, CHCl3)
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChI
- 1S/C20H28O4/c1-13-11-15-16-18(2,17(21)24-15)7-4-8-19(16,3)20(13,22)9-5-14-6-10-23-12-14/h6,10,12-13,15-16,22H,4-5,7-9,11H2,1-3H3/t13-,15-,16+,18+,19+,20-/m1/s1
- InChIKey
- HQLLRHCTVDVUJB-OBHOOXMTSA-N
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
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- WGK 3
- ridadr
- 2811
- risk_code
- 25
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 1-22-45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Applications
UsesMarrubiin is an α-glucosidase inhibitor and an analgesic compound.
Additional notes
DefinitionChEBI: Marrubiin is a gamma-lactone.
Suppliers
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Compound notes
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