Damascenone is an active compound of Epipremnum pinnatum which has anti-inflammatory properties. E-isomer- and Z-isomer-Damascenone combine to form the compound known as damascenone.

Physicochemical Properties

Molecular Formula	C13H18O
Molecular Weight	190.28142
Exact Mass	190.135
CAS #	23696-85-7
Related CAS #	23696-85-7
PubChem CID	5366074
Appearance	Colorless to light yellow liquid
Density	0.9±0.1 g/cm3
Boiling Point	275.6±10.0 °C at 760 mmHg
Flash Point	111.0±14.0 °C
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.491
LogP	4.04
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Heavy Atom Count	14
Complexity	327
Defined Atom Stereocenter Count	0
SMILES	C/C=C/C(C1=C(C)C=CCC1(C)C)=O
InChi Key	POIARNZEYGURDG-FNORWQNLSA-N
InChi Code	InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
Chemical Name	(E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
Synonyms	Damascenone; (E/Z)-Damascenone
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

Targets	Human Endogenous Metabolite
ln Vitro	Immune assays for cell surface E-selectin and secreted TNF-α showed that β-Damascenone also inhibits the upregulation of inflammatory proteins[1]. In vitro, when human cellular systems are activated by various inflammatory stimuli, β-Damascenone inhibits the NF-κB signaling pathway[1].
References	[1]. C13 Megastigmane Derivatives From Epipremnum pinnatum: β-Damascenone Inhibits the Expression of Pro-Inflammatory Cytokines and Leukocyte Adhesion Molecules as Well as NF-κB Signaling.
Additional Infomation	Beta-damascenone is a cyclic monoterpene ketone that is 2,6,6-trimethylcyclohexa-1,3-diene substituted at position 1 by a crotonoyl group. It has a role as a fragrance, a volatile oil component and a plant metabolite. It is an enone, an apo carotenoid monoterpenoid and a cyclic monoterpene ketone. Damascenone has been reported in Camellia sinensis, Malus, and other organisms with data available. 1-[2,6,6-Trimethyl-1,3-cyclohexadien-1-yl]-2-buten-1-one is a metabolite found in or produced by Saccharomyces cerevisiae. trans-beta-damascenone is a metabolite found in or produced by Saccharomyces cerevisiae.

Solubility Data

Solubility (In Vitro)

DMSO: ~100 mg/mL (~525.5 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (13.14 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.14 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (13.14 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	5.2554 mL	26.2771 mL	52.5541 mL
	5 mM	1.0511 mL	5.2554 mL	10.5108 mL
	10 mM	0.5255 mL	2.6277 mL	5.2554 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.