591-12-8 Usage
Description
α-Angelica lactone, a cyclic lactone naturally found in tobacco, is known for its sweet, herbaceous odor reminiscent of tobacco. It is characterized by its unique taste profile, which includes sweet, creamy, coconut, vanilla hay, and coumarin-like nuances at a concentration of 100 ppm. alpha-Angelica lactone is also reported to be present in grape, white bread, soybean, and licorice.
Uses
Used in Cancer Chemoprevention:
α-Angelica lactone serves as a cancer chemopreventive agent, playing a crucial role in the synthesis of glutathione and the activity of detoxification enzymes such as glutathione-S-transferase and UDP-glucuronosyltransferase in various organs, including the esophagus, stomach, intestine, and liver.
Used in Tobacco Flavoring:
In the tobacco industry, α-Angelica lactone is utilized as a flavoring agent due to its natural occurrence in tobacco and its sweet, herbaceous odor that resembles the characteristic taste of tobacco.
Used in Oral Care Formulations:
α-Angelica lactone is employed in oral care formulations to enhance and round out the mint notes, providing a pleasant and refreshing taste experience.
Used in Coffee Flavors:
alpha-Angelica lactone is also used in the flavor industry, specifically for adding depth and complexity to coffee flavors, contributing to a richer and more enjoyable taste.
Preparation
By dry distillation of levulinic acid
Biochem/physiol Actions
Plant-derived cancer chemopreventive agent. Increases the synthesis of glutathione and the activity of glutathione-S-transferase and UDP-glucunonosyltransferase detoxification enzymes in esophagus, stomach, intestine, and liver.
Safety Profile
Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits acrid smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 591-12-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 1 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 591-12:
(5*5)+(4*9)+(3*1)+(2*1)+(1*2)=68
68 % 10 = 8
So 591-12-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H6O2/c1-4-2-3-5(6)7-4/h2H,3H2,1H3
591-12-8Relevant articles and documents
Renewable bio-based routes to γ-valerolactone in the presence of hafnium nanocrystalline or hierarchical microcrystalline zeotype catalysts
Antunes, Margarida M.,Fernandes, Auguste,Pillinger, Martyn,Ribeiro, Filipa,Silva, Andreia F.,Valente, Anabela A.
, p. 56 - 71 (2022/01/19)
Different renewable bio-based routes leading to the versatile bioproduct γ-valerolactone (GVL) were studied in integrated fashions, starting from furfural (Fur), α-angelica lactone (AnL) and levulinic acid (LA), in the presence of multifunctional hafnium-
Synthesis of renewable alkylated naphthalenes with benzaldehyde and angelica lactone
Cong, Yu,Li, Guangyi,Li, Ning,Wang, Aiqin,Wang, Ran,Wang, Xiaodong,Xu, Jilei,Zhang, Tao
supporting information, p. 5474 - 5480 (2021/08/16)
Herein, we report a new route for the synthesis of renewable alkylated naphthalenes (ANs) with benzaldehyde and angelica lactone, two platform compounds that can be derived from lignocellulose.
Regioselective β-Arylation of α-Angelica Lactone through Isomerization/Addition under Mild Conditions
Zhuo, Kai-Feng,Yu, Shang-Hai,Gong, Tian-Jun,Fu, Yao
, p. 693 - 697 (2020/02/04)
The conversion of biomass-based platform molecules into various high-value chemicals greatly promotes the utilization of renewable biomass resources. Herein, an example of Rh-catalyzed β-arylation of levulinic-acid-derived α-angelica lactone was reported, providing the γ-lactone-structure products with high regioselectivity. Both arylboronic and alkenylboronic acids could be applied in this transformation. This reaction tolerated a variety of synthetically important functional groups. Moreover, the obtained γ-lactone products could be readily converted to high-value products such as 1,4-diols and γ-methoxy-carboxylates.
