Alpha-Angelica lactone

Names

[ CAS No. ]:
591-12-8

[ Name ]:
Alpha-Angelica lactone

[Synonym ]:
D2-Angelica lactone
δ2-Angelica lactone
EINECS 209-701-8
5-methyl-3H-furan-2-one
α-Angelica lactone
2(3H)-Furanone, 5-methyl-
5-Methylfuran-2(3H)-one
g-Methyl-b,g-crotonolactone
alpha-Angelica lactone
MFCD00005375
5-Methyl-2(3H)-furanone
4-Hydroxy-3-pentenoic acid γ-lactone
a-Angelic lactone
a-Angelica Lactone
4-Hydroxy-3-pentenoic acid g-lactone

Biological Activity

[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].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Metabolic Enzyme/Protease >> Gutathione S-transferase

[Target]

Glutathione-S-thansferase (GST) detoxification enzyme[1][2] UDP-glucononosyltransferase (UGT) detoxification enzyme[2]

[References]

[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.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
249.4±9.0 °C at 760 mmHg

[ Melting Point ]:
13-17 °C(lit.)

[ Molecular Formula ]:
C₅H₆O₂

[ Molecular Weight ]:
98.100

[ Flash Point ]:
68.3±0.0 °C

[ Exact Mass ]:
98.036781

[ PSA ]:
26.30000

[ LogP ]:
0.84

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.472

[ Water Solubility ]:
5 g/100 mL (25 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LU5075000

CHEMICAL NAME :: 2(3H)-Furanone, 5-methyl-

CAS REGISTRY NUMBER :: 591-12-8

BEILSTEIN REFERENCE NO. :: 0108394

LAST UPDATED :: 199710

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C5-H6-O2

MOLECULAR WEIGHT :: 98.11

WISWESSER LINE NOTATION :: T5OV CHJ E1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3900 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0571138

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 3,249,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 2,109,1946

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NA 1993 / PGIII

[ WGK Germany ]:
2

[ RTECS ]:
LU5075000

[ HS Code ]:
2932209090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932209090

[ Summary ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Characterization of the PON1 active site using modeling simulation, in relation to PON1 lactonase activity

Bioorg. Med. Chem. 16 , 7504-9, (2008)

Paraoxonase1 (PON1) is a HDL bound enzyme and many of the anti-atherogenic properties of HDL are attributed to PON1. The enzyme precise mechanism of protective action and its endogenous substrate rema...

Enhancement of rat hepatic and gastrointestinal glutathione and glutathione S-transferases by alpha-angelicalactone and flavone.

Carcinogenesis 16(3) , 607-12, (1995)

The naturally occurring anticarcinogens flavone and alpha-angelicalactone incorporated separately and simultaneously in the diet at 0.5, 0.1, 0.05 and 0.01% w/w, were studied with respect to their eff...

Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated α-angelica lactone.

Org. Lett. 13(12) , 3056-9, (2011)

A direct highly diastereo- and enantioselective asymmetric vinylogous Mannich-type (AVM) reaction of aldimines with nonactivated natural α-angelica lactone has been successfully developed. It was demo...