Perilla ketone

Furan, 3-(4-methylpentanoyl) — see Perilla ketone Furan, 2-methylthio-mass spectrometry, 4, 583 Furan, 3-morpholino-2,5-diphenyl-reaotions... 

Perilla ketone — see Ketone, 3-furyl isopentyl Perillene synthesis, 4, 668 Perinones, 1, 327, 337 Periodinane, bromo-synthesis, 1, 571 Periodinane, difluoro-reactions, 1, 571 Periodinanes cyclic... 

Acylation reactions can also be greatly improved in this way, with t-alkyl- or sec-alkyl-manganese reagents reacting with acid chlorides in excellent yields [123]. The related addition-elimination to 3-ethoxy-2-cyclohexenone is also improved, resulting after acidic aqueous workup in 3-methyl-2-cyclohexenone [125]. The perilla-ketone 126 was prepared in an improved yield using copper(I) catalysis (Scheme 2.58) [129]. 

Scheme 2.S8. Preparation of perilla-ketone using copper-catalyzed acylation.

It was found that 3-phenylthiopropanal ethylene acetal (50) is a useful starting material for the preparation of 3-acylfurans (79CL709). Several 3-acylfurans have been discovered in nature (B-59MI31200) but few syntheses have been reported (77JOC1089) except those starting from a 3-substituted furan. Some 3-acylfurans, including perilla ketone, 3-(4-methylpentanoyl)furan, have now been prepared from the acetal (50) and an N-acylaziridine, or an aldehyde and subsequent oxidation. Deacylation reactions are suppressed by the use of 3-phenylthiopropanal ethylene acetal (50), and it affords the desired... 

Cis Dimethylfuranoid esters such as (29) have been isolated from the lipid extracts of some fish species (81CC1110). A naturally occurring 3-acylfuran named perilla ketone (53 R = /-CsHn) has been isolated from Perilla frutescens Brit. (79CL709), while 9,10-dehydrofuranoeremophilane (56) is one of the furanoeremophilanoid constituents isolated from Senecio teretifolins DC (80JCS(P1)963). 

Sodium phenobarbital Oxathiin carboxanilide Physostigmine Perilla ketone (NSC 348407) Peptides Somatotropin Physostigmine Etoposide Bleomycin... 

Paborji, M., Riley, C.M., and Stella, V.J. (1988) A novel use of Intralipid for the parenteral delivery of perilla ketone (NSC-348407), an investigational cytotoxic drug with a high af nity for plhsttid. Pharm.,... 

An analysis of oil from Per ilia frutescens var. acuta is reported, but the abstract mentions only perilla ketone (324) and other well-known substances, so it is difficult to assess the novelty of the work. ... 

Wilson et al. (39) isolated the toxin, perilla ketone, which causes pulmonary edema (fluid in the lung cavity) in many animal species, although not in pigs and dogs (40). In Japan, 20-50% of long-term workers in the perilla industry developed dermatitis on their hands because of contact with perillaldehyde (41). Small amounts of these components have been detected in perilla oil where it works as an efficient antioxidant. 

Acylfurans 2- and 3-Acylfurans can be prepared in excellent yield by reaction of furoyl chlorides with RMnCl catalyzed by CuCl. This reaction can provide the natural furanyl ketones naginata ketone (I) and perilla ketone (2). 

Perilla Ketone. l-(3-Furanyl)-4-methyl-l-penta-none l-(3-furyl)-4-meihyl-l-pentanone 0-turyl isoamyt ketone. C HmO, mol wt 166.22. C 72.26%. H 8.49%. O 19.25%. Potent pulmonary edcmatogenjc agent in animals. Isoln from the mint plant, Perilla fruteseens Britton, Labi-atae, and structure R. Goto, J. Pharm. Soc. Japan 57, 77 (1937). Synthesis T. Matsuura, Bull Chem. Soc, Japan 30, 430 (1957) K. Rondo, M. Matsumoto, Tetrahedron Letters 1976, 4363 T. Kitamura et of., Synth. Common. 7, 521 (1977) K. Inomata et al, Chem. Letters 1979, 709. Potent lung toxin implicated in emphysema of grazing cattle B. I. Wilson et al. Science 197, 573 (1977). 

The furan ring is found in furoic acid (3.38). Some alkyl furan derivatives have value as odorants. Thus, rose furan (3.39) gives the characteristic odor of rose oil. Other derivatives have potent biological activity, such as beta-furyl isoamyl ketone (perilla ketone, 3.40), which causes pulmonary edema in animals grazing on plants containing this substance (such as Perilla Frutescens Britton). Ascorbic acid (the well-known Vitamin C), which when written as the enoUc form (3.42) is... 

Perilla frutescens can be class ed in several chemotypes as well according to the main mono-terpene components perillaldehyde, elsholtzia ketone, or perilla ketones and on the other side phenylpropanoid types containing myristicin, dillapiole, or elemicin (Koezuka et al., 1986). A comprehensive presentation on the chemotypes and the inheritance of the mentioned compounds was given by this author in Hay and Waterman (1993). In the referred last two examples, not only the sensorial but also the toxicological properties of the essential oil compounds are decisive for the (further) commercial use of the respective species biodiversity. 

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