CAS 591-12-8|Alpha-Angelica lactone
| Common Name | Alpha-Angelica lactone | ||
|---|---|---|---|
| CAS Number | 591-12-8 | Molecular Weight | 98.100 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 249.4±9.0 °C at 760 mmHg |
| Molecular Formula | C5H6O2 | Melting Point | 13-17 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 68.3±0.0 °C |
Names
| Name | α-angelica lactone |
|---|---|
| Synonym | More Synonyms |
Alpha-Angelica lactone BiologicalActivity
| 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 >>CancerSignaling 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 |
| InChIKey | QOTQFLOTGBBMEX-UHFFFAOYSA-N |
| SMILES | CC1=CCC(=O)O1 |
| Water Solubility | 5 g/100 mL (25 ºC) |
Toxicological Information
CHEMICAL IDENTIFICATION |
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 |
Customs
| HS Code | 2932209090 |
|---|---|
| Summary | 2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Articles5
More 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... |
Synonyms
| 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 |
