Dill weed oil

Fragrance raw materials monographs DILL

WEED

747

OIL

Synonyms:Dill oil; dill herb oil. Descriptionand physical properties: Merck Index (1968).The constituentsof dill weedoil have been reported aspredominantlyd-a-phellandreneand carvone (Guenther, 1950),as mainly phellandrene together with limoneneor dipeatene,d-carvone(in much smallerquantitiesthan in dill seedoil), and myristicin (Appell, 1968)and, in the caseof the oil from Anethum graueolens, as d-a-phellandrene, limonene,terpineneand a-pinenewith smallamountsof carvone,dillapiole,myristicin and isomyristitin (Karow, 1969).The oil from the tops of Indian A. graueolens was found by Baslas& Baslas (1972)to contain (in ml/100ml) limonene(12),a-terpinene(14), a-phellandrene(9), methyl benzoate (25), dihydrocarvone(7), carvone (13), carveol (4), &role (2.4), dihydrocarveol (2.7), carvacrol (3), eugenol(5), sesquiterpenes (10) and dillapiole 2.5. Dill greens(American A. graoeolens) contained d-carvoneandmyristicin, but not apiole and dillapiole,which werepresentin the roots (Lichtenstein, Liang, Schultz, Schnoes& Carter, 1974).Dill weedoil containssizeableamountsof the psychotropic substance myristicin; isomyristicinand dillapiolearepresentwith myristicin in A. graueolens (Shulgin, 1966).The fatty acid compositionof the essentialoils from the above-groundparts and from the fruit of A. graueolens was studied by Narzieva, Stepanenko,Umarov & Maksudov (1974),and seasonalchangesin the quantity and compositionof the essentialoil from A. graueolens flowers, leavesand stemswere studiedby Zlatev 8~Balinova-Tsvetkova(1974). Occurrence: Found in the plant of A. graueolens, L. (Fam. Umbelliferae)(Guenther, 1950). Preparation: By steamdistillation of the freshly cut plants of A. graueolens L. (Guenther, 1950). Uses:In public usebeforethe 1870s.Usein fragrancesin the USA amountsto lessthan lOOOlb/yr. Concentrationin final product (%): Soap

Usual Maximum Analytical

0.01 0.1

Detergent

Creams, lotions

0.001 0.01

Perfume

0405

@04

003

0.4

data: Gas chromatogram,RIFM no. 75-36; i&a-red curve, RIFM no. 75-36.

Dill oil was given GRAS status by FEMA (1965)and is approved by the FDA for food use (GRAS). The Council of Europe (1974)includeddill in the list of substances, spicesand seasonings deemedadmissiblefor use with a possiblelimitation of the active principle in the final product. The Food Chemicals Codex (1972)hasa monographon dill oil. Biological

data

Acute toxicity. The acuteoral LD,, value in rats wasreportedas4.04ml/kg and the acute dermal LD,,, value in rabbits as> 5 g/kg (Levenstein,1975). Irritation. Undiluted dill weedoil was not irritating when appliedto the backs of hairlessmice and swine(Urbach & Forbes,1975).or to intact or abradedrabbit skin for 24hr under occlusion (Levenstein,1975).Testedat 4% in petrolatum, it producedno irritation after a 48-hr closed-patch test on human subjects(Kligman, 1975). Sensitization. A maximization test (Kligman, 1966; Kligman & Epstein, 1975)was carried out on 25 volunteers.The material was testedat a concentration of 4% in petrolatum and produced no sensitizationreactions(Kligman, 1975).The dill plant hasbeenreported to be a photosensitizing agent(Stempel& Stempel,1973). Phototoxicity. No phototoxic effectswere reported for undiluted dill weedoil on hairlessmice and swine(Urbach & Forbes,1975). Medicinal uses. Usedas an aromatic carminativein medicines(Merck Index, 1968). Pharmacology. Dill oil from parts of the A. graueolens plant at concentrationsof SO-lOOpg/ml had a spasmolyticeffect on smoothmuscle(isolatedrabbit and guinea-pigintestineand guinea-pig lung) and a 5%emulsionin physiologicalsalinegiven iv to cats at 5-10mg/kg increasedrespiratory volume and depressedblood pressure(Shipochliev,1968).The spasmolyticeffect was considered to be chiefly myotropic. In nearly 100 haemorrhoidalpatients,one-third of whom were yotmg, repeatedoral dosesand nightly enemasof an aqueousinfusion preparedfrom 20-25 g dill plant (A. graueolens) in 200-250g water causedcompleteand lasting reduction of venousknots in 2-3 wk (Freise,1938). Insects. Crude dill green extracts from A. graueolens were active as insecticidesand insecticide synergistsbecauseof their content of d-carvoneand myristicin (Lichtensteinet al. 1974). Micro-organisms. Oil from dill plants, A. graueolens, inhibited the growth of Bacillus subrilis in a 1:320 dilution and of Staphylococcus aureus in a 1:160 dilution, but did not affect the growth of Escherichia coli. It also inhibited the growth of Aspergillus oryzae but not of two other fungi (Dovgich, 1971).In testsusingthe filter-paper-discmethod,dill weedoil inhibitedthe in uitro growth of all of a group of three wood-destroyingfungi (Maruzzella, Scrandis,Scrandis,& Grabon, 1960)

D. L. J. OPDYKE

748

and all of a group of 12 phytopathogenic fungi (Maruzzella & Balter, 1959), but only one of a group of ten pathogenic and non-pathogenic bacteria was affected (Maruzzella & Lichtenstein, 1956). The vapour of dill weed oil inhibited the in vitro growth of one of a group of four bacteria (Maruzzella & Sicurella, 1960). References

Appell, L. (1968). Physical foundations in perfumery. VI. Volatility of the essential oils. Am. PerjGner Cower. 83(11). 37. Baslas, B. K. u...Baslas, R. K. (1972). Chemische Untersuchung des aus dem Kraut von Anethum graveolens gewonnenen Oles. Reichstoffe Arom. 22(S), 155. Council of Europe (1974), Natural Flavouring Substances, Their Sources, and Added Artificial Flavouring Substances. Partial Agreement in the Social and Public Health Field. List N(l), Series l(b), no. 42, p. 39. Strasbourg. Dovgich, N. A. (1971). Antimicrobial effect of essential oils. Mikrobiol. Zh. A.N.U.R.S.R. 33, 253. Flavoring Extract Manufacturers’ Association (1965). Survey of 5avoring ingredient usage levels. No. 2383. Fd Technol., Champaign M(2), part 2, 155. Food Chemicals Codex (1972). 2nd Ed. Prepared by the Committee on Specifications, Food Chemicals Codex, of the Committee on Food Protection. p. 250. National Academy of Sciences-National Research Council Publ. 1406, Washington, D.C. Freise, F. W. (1938). Zubereitungen von Dill (Anetbum graveolens L.) als Antihaemorrhoidlia. Pharm Zentralh. 79. 636. Guenther, E. (1950). The Essential Oils. Vol. IV, p. 619. D. Van Nostrand, Inc., Princeton, New Jersey. Karow, H. (1969). Quality-determining components of some spices. II. Riechstofi Arom. N(2), 60. Kligman, A. M. (1966). The identification of contact allergens by human assay. III. The maximization test. A procedure for screening and rating contact sensitizers. J. invest. Derm. 47, 393. Kligman, A. M. (1975). Report to RIFM, 27 March. Kligman, A. M. & Epstein, W. (1975). Updating the maximization test for identifying contact allergens. Contact

Dermatitis

1, 231.

Levenstein, I. (1975). Report to RIFM. 31 January. Lichtenstein, E. P., Liang, T. T., SchultG K. R., Schnoes, H. K. & Carter, G. T. (1974). Insecticidal and synergistic components isolated from dill plants. J. agric. Fd Chem. 22, 658. Maruuella, J. C. & Balter, J. (1959). The action of essential oils on phytopathogenic fungi. PI. Dis. Reptr 43, 1143. Maruzzella, J. C. & Lichtenstein, M. B. (1956). The in vitro antibacterial activity of oils. J. Am. pharm. Ass. 45, 378.

Maruzzella, J. C., Scrandis, D. A., Scrandis, J. B. & Grabon, G. (1960). Action of odoriferous organic chemicals and essential oils on wood-destroying fungi. PI. Dis. Reptr 44, 789. Maruzzella, J. C. & Sicurella, N. A. (1960). Antibacterial activity of essential oil vapors. J. Am. pharm. Ass. 49, 692. Merck Index

(1968). An Encyclopedia of Chemicals and Drugs. 8th Ed., p. 758. Merck & Co., Inc., Rahway, New Jersey. Narzieva, M. D., Stepanenko, G. A., Umarov, A. U. & Maksudov, N. Kh. (1974). Oils from An&hum graveolens. Khimiya

prirod.

Soedin.

10, 243.

Shipochhev, T. (1968). Pharmacological investigation into several essential oils. I. Effect on the smooth musculature. VetMed. Nauki S(6), 63. Shulgin, A. T. (1966). Possible implication of myristicin as a psychotropic substance. Nature, Land. 210, 380. Stempel. E. & Stempel, R. (1973). Drug-induced photosensitivity. J. Am. pharm. Ass. 13, 200. Urbach, F. & Forbes, P. D. (1975). Report to RIFM, 28 February. Zlater, S. & Balinova-Tsvetkova, A. (1974). Dynamics of essential oil accumulation in dill (Anethum graveolens). Rastenieuud. Nauki 11(3), 69.