α-Angelica lactone is a naturally occurring anti-cancer compound and a vinyl nucleophile. α-Angelica lactone can give chiral δ-aminoγ, γ-disubstituted butenol lactone carbonyl analogues and exhibit electrophilic trapping on the γ-carbon. α-Angelica lactone exerts potent chemoprotective effects by selectively enhancing glutathione-S-sulfotransferase (GST) and UDP-glucosyltransferase (UGT) detoxification enzymes.

Physicochemical Properties

Molecular Formula	C₅H₆O₂
Molecular Weight	98.10
Exact Mass	98.036
CAS #	591-12-8
PubChem CID	11559
Appearance	Colorless to light yellow liquid
Density	1.1±0.1 g/cm3
Boiling Point	249.4±9.0 °C at 760 mmHg
Melting Point	13-17 °C(lit.)
Flash Point	68.3±0.0 °C
Vapour Pressure	0.0±0.5 mmHg at 25°C
Index of Refraction	1.472
LogP	0.84
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Heavy Atom Count	7
Complexity	124
Defined Atom Stereocenter Count	0
SMILES	CC1=CCC(=O)O1
InChi Key	QOTQFLOTGBBMEX-UHFFFAOYSA-N
InChi Code	InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2H,3H2,1H3
Chemical Name	5-methyl-3H-furan-2-one
Synonyms	αAngelica lactone; α Angelica lactone
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: Please store this product in a sealed and protected environment, avoid exposure to moisture.
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]. Quantification of Induction of Rat Oesophageal, Gastric and Pancreatic Glutathione and Glutathione S-transferases by Dietary Anticarcinogens. Carcinogenesis. 1994 Sep;15(9):1769-72. [2]. Induction of Rat Hepatic and Intestinal UDP-glucuronosyltransferases by Naturally Occurring Dietary Anticarcinogens. Carcinogenesis. 2003 Oct;24(10):1651-6. [3]. Catalytic Asymmetric Vinylogous Mannich-type (AVM) Reaction of Nonactivated α-Angelica Lactone. Org Lett. 2011 Jun 17;13(12):3056-9. [4]. Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters. J Org Chem. 2017 Feb 17;82(4):2276-2280.

Additional Infomation

Alpha-angelica lactone is an angelica lactone and a butenolide. It is functionally related to a but-3-en-4-olide. It is a tautomer of a beta-angelica lactone. alpha-Angelica lactone has been reported in Picea abies, Arctostaphylos uva-ursi, and Tamarindus indica with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~1019.37 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (25.48 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 (25.48 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 (25.48 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	10.1937 mL	50.9684 mL	101.9368 mL
	5 mM	2.0387 mL	10.1937 mL	20.3874 mL
	10 mM	1.0194 mL	5.0968 mL	10.1937 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.