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α-Angelica lactone

CAT: 0804-HY-N0548-01Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0548-01Size:500 mg
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Description
α-Angelica lactone is a naturally occurring anticarcinogen and an vinylogous nucleophile. α-Angelica lactone can give the chiral δ-amino γ, γ-disubstituted butenolide carbonyl derivatives and exhibitselectrophilic trapping at the γ-carbon. α-Angelica lactone exerts strong chemoprotective effects by selective enhancement of glutathione-S-thansferase (GST) and UDP-glucononosyltransferase (UGT) detoxification enzymes[1][2][3][4].
CAS Number
591-12-8
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Glutathione S-transferase
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/α-angelica-lactone.html
Purity
99.93
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C1OC(C)=CC1
Molecular Formula
C5H6O2
Molecular Weight
98.10
Precautions
H302, H315, H319, H335
References & Citations
[1]W A Nijhoff, et al. 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]E M J van der Logt, et al. Induction of Rat Hepatic and Intestinal UDP-glucuronosyltransferases by Naturally Occurring Dietary Anticarcinogens. Carcinogenesis. 2003 Oct;24 (10) :1651-6.|[3]Lin Zhou, et al. Catalytic Asymmetric Vinylogous Mannich-type (AVM) Reaction of Nonactivated α-Angelica Lactone. Org Lett. 2011 Jun 17;13 (12) :3056-9.|[4]Jessica A Griswold, et al. Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters. J Org Chem. 2017 Feb 17;82 (4) :2276-2280.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

alpha-Angelica lactone

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.

CAS Number591-12-8
PubChem CID11559
IUPAC Name5-methyl-3H-furan-2-one
Molecular FormulaC5H6O2
Molecular Weight98.10
XLogP0.6
Topological Polar Surface Area26.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Heavy Atom Count7
Formal Charge0
Complexity124
SMILES
CC1=CCC(=O)O1
InChI
InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2H,3H2,1H3
InChIKey
QOTQFLOTGBBMEX-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of alpha-Angelica lactone
CAS: 591-12-8
CID: 11559
Formula: C5H6O2
MW: 98.10
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight98.10
XLogP30.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass98.036779430
Monoisotopic Mass98.036779430
Topological Polar Surface Area26.3 Ų
Heavy Atom Count7
Formal Charge0
Complexity124
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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