41678-29-9

Basic information

• Product Name: Edulan I
• Synonyms: Edulan I
• CAS NO: 41678-29-9
• Molecular Formula: C13H20O
• Molecular Weight: 192.3
• Mol File: 41678-29-9.mol

Chemical Properties

• Boiling Point: 256.3±39.0 °C(Predicted)
• Appearance: /
• Density: 0.96±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Edulan I(CAS DataBase Reference)
• NIST Chemistry Reference: Edulan I(41678-29-9)
• EPA Substance Registry System: Edulan I(41678-29-9)

Safety Data

• Hazardous Substances Data: 41678-29-9(Hazardous Substances Data)

Upstream product

• 14203-64-6 7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one 
• 23526-45-6 6,9-dihydroxymegastigma-4,7-dien-3-one 

Relevant articles and documents

Structure-Odor Correlation, XIX. Synthesis and Olfactory Properties of Various Racemic Theaspirones, Ketoedulans and Edulans

Starting from the cheap isophorone derivative 1 and the alkynols 2-4, we could prepare the key intermediates 9-11 via addition reaction (--> 5-7) and hydrogenation.Ring closure of 9-11 led to the theaspirone (C) and/or ketoedulan (E) series, depending on the reaction conditions used and the steric situation at C-2.By tratment of 9 with tosyl chloride/pyridine the theaspirone derivative 13 was formed exclusively, whereas 10a, b were converted into mixtures of 14a, b together with the ketoedulan derivatives 20a, b; the crowded 11 did not react at all.By treatment of 9-11 with hydrochloric acid/acetone 19-21 were readily obtained.Several hydrogenation and dehydration steps under various conditions led to the theaspirones 16-18, to the ketoedulans 26a, b and 27, and to the edulans 39a and 40b. - Olfactory evaluation of the theaspirones 16 (harsh, green), 17a (floral, fruity) and 18 (weak, woody) shows the drastic influence of the steric situation at C-2.The ketoedulans 26a and 27 smell weak, woody.Evaluation of both odor and flavor of 39a and 40b exhibits mostly woody, camphoraceous and fruity tonalities. - Key Words: Theaspirone derivatives / Edulan derivatives / Terpenes / Odor

New Syntheses of Edulans and Theaspiranes from α-Inone

New syntheses of edulans and theaspiranes are described.The key step involves the cyclization of 4-(2',6',6'-trimethyl-2'-hydroxy-3'-cyclohexen-1'-yl)-butan-2-ol (7) and 4-(2',6',6'-trimethyl-1',2'-dihydroxy-3'-cyclohexen-1'-yl)-butan-2-ol (8) derived from α-ionone.The diol (7) and triol (8) were cyclized with acetic acid into the corresponding tetrahydropyran derivatives ; the latter two compounds were dehydrated to edulan I and II (13a, 13b).On treatment with tosyl chloride in pyridine, however, triol (8) gave spiro-compounds (11a, 11b and 12); (11a and 11b) were easily converted to cis- and trans-theaspirone by oxidation and 5,6-erythro-6-hydroxy-dihydrotheaspiranes (15a and 15b) by reduction.