Marrubiin can be extracted from Marrubium vulgare and has vasorelaxant and anti-edema activities. Marrubiin also relieves symptoms of diabetes in animals.

Physicochemical Properties

Molecular Formula	C20H28O4
Molecular Weight	332.4339
Exact Mass	332.199
CAS #	465-92-9
PubChem CID	73401
Appearance	White to off-white solid powder
Density	1.152g/cm3
Boiling Point	465.2ºC at 760mmHg
Melting Point	159-162ºC
Flash Point	235.2ºC
Vapour Pressure	1.87E-09mmHg at 25°C
Index of Refraction	1.537
LogP	3.721
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Heavy Atom Count	24
Complexity	534
Defined Atom Stereocenter Count	6
SMILES	C[C@@H]1C[C@@H]2[C@H]3[C@](CCC[C@@]3([C@]1(CCC4=COC=C4)O)C)(C(=O)O2)C
InChi Key	HQLLRHCTVDVUJB-OBHOOXMTSA-N
InChi Code	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
Chemical Name	(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
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References	[1]. The vasorelaxant activity of marrubenol and marrubiin from Marrubium vulgare. Planta Med. 2003 Jan;69(1):75-7. [2]. Antioedematogenic effect of marrubiin obtained from Marrubium vulgare. J Ethnopharmacol. 2006 Dec 6;108(3):379-84. [3]. Marrubiin, a constituent of Leonotis leonurus, alleviates diabetic symptoms. Phytomedicine. 2012 Apr.
Additional Infomation	Marrubiin is a gamma-lactone. Marrubiin has been reported in Marrubium globosum, Marrubium trachyticum, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~300.82 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.52 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.0082 mL	15.0408 mL	30.0815 mL
	5 mM	0.6016 mL	3.0082 mL	6.0163 mL
	10 mM	0.3008 mL	1.5041 mL	3.0082 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.