Poppyseed oil (also poppy seed oil, poppy oil, and oleum papaveris seminis) is an edible oil Cooking oil is purified fat of plant origin, which is usually liquid at room temperature from poppy seeds Poppy seed is an oilseed obtained from the opium poppy . The tiny kidney-shaped seeds have been harvested from dried seed pods by various civilizations for thousands of years. The seeds are used, whole or ground, as an ingredient in many foods, and they are pressed to yield poppyseed oil (seeds A seed ( /ˈsiːd/ ) is a small embryonic plant enclosed in a covering called the seed coat, usually with some stored food. It is the product of the ripened ovule of gymnosperm and angiosperm plants which occurs after fertilization and some growth within the mother plant. The formation of the seed completes the process of reproduction in seed of Papaver somniferum Opium poppy, Papaver somniferum var. album, is the species of plant from which opium and poppy seeds are extracted. Opium is the source of many opiates, including morphine, thebaine, codeine, papaverine, and noscapine. The Latin botanical name means, loosely, the "sleep-bringing poppy, white form", referring to the narcotic property of, the opium poppy The poppy is the only species of Papaveraceae that is an agricultural crop grown on a large scale. Other species, Papaver rhoeas and Papaver argemone, are important agricultural weeds, and may be mistaken for the crop). The oil has culinary and pharmaceutical uses, as well as long established uses in the making of paints, varnishes, and soaps.

Poppy seeds yield 45–50% oil.[1] Like poppy seeds, poppyseed oil is highly palatable Flavor or flavour is the sensory impression of a food or other substance, and is determined mainly by the chemical senses of taste and smell. The "trigeminal senses", which detect chemical irritants in the mouth and throat, may also occasionally determine flavor. The flavor of the food, as such, can be altered with natural or artificial, high in vitamin E Vitamin E is a generic term for tocopherols and tocotrienols. Vitamin E is a family of α-, β-, γ-, and δ- tocopherols and corresponding four tocotrienols. Vitamin E is a fat-soluble antioxidant that stops the production of reactive oxygen species formed when fat undergoes oxidation. Of these, α-tocopherol (also written as alpha-tocopherol), and has no narcotic The term narcotic strictly refers (medically) to any psychoactive compound with morphine-like effects (see Opiate). A Narcotic is defined as a drug such as opium or morphine that in moderate doses relieves pain and induces deep sleep. Excessive use can cause tremors and seizures. However, the term is also used colloquially to refer to any properties.

Contents

Chemistry

Poppy seeds are notable for being especially high in tocopherols Tocopherols are a class of chemical compounds of which many have vitamin E activity. It is a series of organic compounds consisting of various methylated phenols. Because the vitamin activity was first identified in 1936 from a dietary fertility factor in rats, it was given the name "tocopherol" from the Greek words “τόκος” [ other than vitamin E (alpha-tocopherol). Poppyseed oil from one source has been reported to contain 30.9 mg gamma-tocopherol per 100 g.[2] It also contains alpha and gamma tocotrienols Tocotrienols are members of the vitamin E family. An essential nutrient for the body, vitamin E is made up of four tocopherols and four tocotrienols (alpha, beta, gamma, delta). Chemically, vitamin E is an antioxidant. One model for the function of vitamin E in the body is that it protects cell membranes, active enzyme sites, and DNA from free, but not others.[2] Compared to other vegetable oils Vegetable fats and oils are lipid materials derived from plants. Physically, oils are liquid at room temperature, and fats are solid. Chemically, both fats and oils are composed of triglycerides, as contrasted with waxes which lack glycerin in their structure. Although many different parts of plants may yield oil, in commercial practice, oil is, poppyseed oil has a moderate amount of phytosterols Phytosterols are a group of steroid alcohols, phytochemicals naturally occurring in plants. Phytosterols occur naturally in small quantities in vegetable oils, especially sea buckthorn oil (1640 mg/100g oil), corn oil (968 mg/100g), and soybean oil (327 mg/100g oil). One such phytosterol complex, isolated from vegetable oil, is cholestatin,: higher than soybean oil In processing soybeans for oil extraction and subsequent soy flour production, selection of high quality, sound, clean, dehulled yellow soybeans is very important. Soybeans having a dark colored seed coat, or even beans with a dark hilum will inadvertently leave dark specks in the flour, and are undesirable for use in commercial food products. All and peanut oil Peanut oil is an organic material oil derived from peanuts, noted to have the aroma and taste of its parent legume. In the UK it is marketed as "groundnut oil", lower than safflower oil Safflower is a highly branched, herbaceous, thistle-like annual, usually with many long sharp spines on the leaves. Plants are 30 to 150 cm tall with globular flower heads (capitula) and commonly, brilliant yellow, orange or red flowers which bloom in July. Each branch will usually have from one to five flower heads containing 15 to 20 seeds per, sesame oil Sesame oil is an edible vegetable oil derived from sesame seeds. Besides being used as a cooking oil in South India, it is often used as a flavor enhancer in Chinese, Korean, and to a lesser extent Southeast Asian cuisine, wheat germ oil Wheat germ oil is extracted from the germ of the wheat kernel, which makes up only 2½% by weight of the kernel. Wheat germ oil is particularly high in octacosanol[citation needed] - a 28 carbon long-chain saturated primary alcohol found in a number of different vegetable waxes. Octacosanol has been studied as an exercise and physical performance, corn oil Corn oil is oil extracted from the germ of corn . Its main use is in cooking, where its high smoke point makes refined corn oil a valuable frying oil. It is also a key ingredient in some margarines.[citation needed] Corn oil is generally less expensive than most other types of vegetable oils.[citation needed] One bushel of corn contains 1.55, and rice bran oil Rice bran oil is the oil extracted from the germ and inner husk of rice. It is notable for its very high smoke point of 490°F and its mild flavor, making it suitable for high-temperature cooking methods such as stir frying and deep frying. It is popular as a cooking oil in several Asian countries, including Japan and China.[3] Sterols Sterols are an important class of organic molecules. They occur naturally in plants, animals, and fungi, with the most familiar type of animal sterol being cholesterol. Cholesterol is vital to cellular function, and a precursor to fat-soluble vitamins and steroid hormones in poppyseed oil consist almost entirely of campesterol Campesterol is a phytosterol whose chemical structure similar to that of cholesterol. Many vegetables, fruits, nuts and seeds contain campesterol, but in low concentrations, stigmasterol Stigmasterol is one of a group of plant sterols, or phytosterols, that include beta-sitosterol, campesterol, ergosterol (provitamin D2), brassicasterol, delta-7-stigmasterol and delta-7-avenasterol, that are chemically similar to animal cholesterol. Phytosterols are insoluble in water but soluble in most organic solvents and contain one alcohol, sitosterol β-Sitosterol is one of several phytosterols with chemical structures similar to that of cholesterol. Sitosterols are white, waxy powders with a characteristic odor. They are hydrophobic and soluble in alcohols and delta 5-avenasterol.[4] Poppyseed oil is high in linoleic acid Linoleic acid is an unsaturated omega-6 fatty acid. It is a colorless liquid at room temperature. In physiological literature, it is called 18:2(n-6). Chemically, linoleic acid is a carboxylic acid with an 18-carbon chain and two cis double bonds; the first double bond is located at the sixth carbon from the omega end. Although not generally higher than safflower oil, it can be as high as 74.5%.[2] Other triglycerides Triglyceride is an ester composed of a glycerol bound to three fatty acids. It is the main constituent of vegetable oil and animal fats present in notable quantities are oleic acid Oleic acid is a mono-unsaturated omega-9 fatty acid found in various animal and vegetable sources. It has the formula CH37CH=CH(CH2)7COOH. The trans-isomer of oleic acid is called elaidic acid and palmitic acid Palmitic acid,CH314COOH or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants. As its name indicates, it is a major component of the oil from palm trees (palm oil, palm kernel oil and coconut oil). The word palmitic is from the French "palmitique", the pith of the palm.[5]

It is less likely than some other oils to become rancid.[1] It is more stable than safflower oil Safflower is a highly branched, herbaceous, thistle-like annual, usually with many long sharp spines on the leaves. Plants are 30 to 150 cm tall with globular flower heads (capitula) and commonly, brilliant yellow, orange or red flowers which bloom in July. Each branch will usually have from one to five flower heads containing 15 to 20 seeds per and linseed oil Linseed oil, also known as flax seed oil, is a clear to yellowish oil obtained from the dried ripe seeds of the flax plant . The oil is obtained by cold pressing, sometimes followed by solvent extraction.[2]

Poppyseed oil is a carrier oil Carrier oil, also known as base oil or vegetable oil, is used to dilute essential oils and absolutes before they are applied to the skin in massage and aromatherapy. They are so named because they carry the essential oil onto the skin. Carrier oils do not contain a concentrated aroma, unlike essential oils, though some, such as olive, have a mild, having little or no odor and a pleasant taste. The primary aroma compound An aroma compound, also known as odorant, aroma, fragrance or flavor, is a chemical compound that has a smell or odor. A chemical compound has a smell or odor when two conditions are met: the compound needs to be volatile, so it can be transported to the olfactory system in the upper part of the nose, and it needs to be in a sufficiently high responsible for its flavor is 2-pentylfuran;[6] also present are the volatile compounds 1-pentanol 1-Pentanol, , is an alcohol with five carbon atoms and the molecular formula C5H12O . 1-Pentanol is a colorless liquid with an unpleasant aroma. There are 7 other structural isomers of pentanol (see amyl alcohol). The ester formed from butanoic acid and 1-pentanol, pentyl butyrate, smells like apricot. The ester formed from acetic acid and 1-, 1-hexanal, 1-hexanol 1-Hexanol is an organic alcohol with a six carbon chain and a condensed structural formula of CH35OH. This colorless liquid is slightly soluble in water, but miscible with ether and ethanol. Two additional straight chain isomers of 1-hexanol exist, 2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group. Many isomeric, and caproic acid.[5]

Uses

In the 19th century The 19th century was a period in history marked by the collapse of the Spanish, Portuguese, Chinese, Holy Roman and Mughal empires. This paved the way for the growing influence of the British Empire, the German Empire and the United States, spurring military conflicts but also advances in science and exploration poppy seed oil was used as cooking oil Cooking oil is purified fat of plant origin, which is usually liquid at room temperature, lamp oil Oil Lamps have traditionally been used as a basic form of lighting, and were widely used as an alternative to candles prior to the era of electric lights. Starting in 1780 the Argand lamp quickly replaced earlier oil lamps still in their basic ancient form. These were, in turn, replaced by the kerosene lamp in about 1850. In small towns and rural, and varnish Varnish is a transparent, hard, protective finish or film primarily used in wood finishing but also for other materials. Varnish is traditionally a combination of a drying oil, a resin, and a thinner or solvent. Varnish finishes are usually glossy but may be designed to produce satin or semi-gloss sheens by the addition of "flatting", and was used to make paints and soaps. Today, all of these uses continue, and poppyseed oil has additional culinary and pharmaceutical uses.[5] Particularly notable are its uses as a carrier for oil paints Oil paint is a type of slow-drying paint that consists of particles of pigment suspended in a drying oil, commonly linseed oil. The viscosity of the paint may be modified by the addition of a solvent such as turpentine or white spirit, and varnish may be added to increase the glossiness of the dried film. Oil paints have been used in England since and as a pharmaceutical grade carrier for medicinal iodine and drugs.

Poppyseed oil was sometimes added to olive and almond oils (see Adulterant Adulterants are chemical substances which should not be contained within other substances . Adulterants may be intentionally added to more expensive substances to increase visible quantities and reduce manufacturing costs, or for some other deceptive or malicious purpose. Adulterants may also be accidentally or unknowingly introduced into).[7] In industrialized countries its most important culinary use these days is as a salad or dipping oil.[8]

Oil painting

Poppyseed oil is a drying oil A drying oil is an oil that hardens to a tough, solid film after a period of exposure to air. The term "drying" is actually a misnomer - the oil does not harden through the evaporation of water or other solvents, but through a chemical reaction in which the components crosslink by the action of oxygen. Drying oils are a key component of. In oil painting Oil painting is the process of painting with pigments that are bound with a medium of drying oil — especially in early modern Europe, linseed oil. Often an oil such as linseed was boiled with a resin such as pine resin or even frankincense; these were called 'varnishes' and were prized for their body and gloss. Other oils occasionally used, it is a popular oil for binding pigment, thinning paint, and varnishing finished paintings. Some users consider "sun-thickened" poppyseed oil to be the best painting medium.[9]

Poppyseed oil is used for painting for at least 1500 years—one of the oldest known oil paintings, found in caves of Afghanistan The Islamic Republic of Afghanistan is a landlocked country in south-central Asia. It is bordered by Pakistan in the south and east, Iran in the west, Turkmenistan, Uzbekistan and Tajikistan in the north, and China in the far northeast. In addition; India claims a border with Afghanistan at the Wakhan corridor as part of its claim on the Gilgit- and dated to 650 AD, was likely drawn using poppyseed oil.[10] It is most often found in white paints,[1] and as a varnish. Painters tended to prepare poppyseed oil by hand, up through the late 19th century The 19th century was a period in history marked by the collapse of the Spanish, Portuguese, Chinese, Holy Roman and Mughal empires. This paved the way for the growing influence of the British Empire, the German Empire and the United States, spurring military conflicts but also advances in science and exploration when oils became available prepared in tubes. While poppyseed oil does not leave the unwanted yellow tint for which linseed oil Linseed oil, also known as flax seed oil, is a clear to yellowish oil obtained from the dried ripe seeds of the flax plant . The oil is obtained by cold pressing, sometimes followed by solvent extraction is known, it dries slower and is less durable than linseed oil.[9]

Contrast agent

Example of iodine-based contrast in cerebral angiography Cerebral angiography is a form of angiography which provides images of blood vessels in and around the brain, thereby allowing detection of abnormalities such as arteriovenous malformations and aneurysms. The technique was pioneered by Egas Moniz in 1927

Iodized poppyseed oil (oil with iodine Iodine , from Greek: ιώδης iodes, meaning violet or purple, is a chemical element that has the symbol I and the atomic number 53 added) has several kinds of pharmaceutical uses. The first of these uses was as a radiocontrast Radiocontrast agents are a type of medical contrast medium used to improve the visibility of internal bodily structures in an X-ray based imaging techniques such as Computed tomography or Radiography (commonly known as X-ray imaging). Radiocontrast agents are typically iodine or barium compounds agent used in medical radiology Radiologists are physicians that utilize an array of imaging technologies (such as ultrasound, computed tomography , nuclear medicine, positron emission tomography (PET) and magnetic resonance imaging (MRI)) to diagnose or treat diseases. Interventional radiology is the performance of (usually minimally invasive) medical procedures with the. The origin of this use is attributed to Jean-Athanase Sicard and Jacques Forestier. Two brand name formulations are ethiodol and lipiodol. These are sterile formulations for medical use that commonly are injected.

These two formulations, and other similarly iodized poppyseed oils, also have multiple applications in the treatment of cancers and iodine deficiencies.

Prevention of iodine deficiency

In some regions where iodized salt Iodised salt is table salt mixed with a minute amount of various iodine-containing salts. The ingestion of iodide prevents iodine deficiency. Worldwide, iodine deficiency affects about two billion people and is the leading preventable cause of mental retardation. It also causes thyroid gland problems, including endemic goitre. In many countries, is not available, iodized poppyseed oil is the standard for preventing iodine deficiency Iodine is an essential trace element; the thyroid hormones thyroxine and triiodotyronine contain iodine. In areas where there is little iodine in the diet—typically remote inland areas where no marine foods are eaten—iodine deficiency gives rise to goiter , as well as cretinism, which results in developmental delays and other health problems and its complications including goiter. It may be given by mouth or by injection, injection being markedly more effective.[11] The origin of this use is attributed to Paulo Campos. Usually it is given to adults and children by intramuscular injection, one injection delivering enough iodine to last 2 or 3 years. Poppyseed oil is used because it is already manufactured and it very rarely causes an allergic reaction. However, injections are more expensive and more difficult to administer than oral medications, thus there is interest in giving iodized oil by mouth. Use by mouth requires only food grade, not medical grade, quality control. A randomized, placebo-controlled clinical trial on giving infants iodized poppyseed oil together with an oral polio vaccine had good results.[12] A randomized, double-blind, fully controlled trial in which lipiodol was given by mouth to children had disappointing results.[13] A recent clinical trial in which iodized oil was given by mouth found that the amount of iodine taken up (see bioavailability) varied with the amount of oleic acid in the oil.[14] Poppyseed oil has relatively little oleic acid. Peanut oil and rapeseed oil have far more oleic acid and are less expensive, and may be superior to poppyseed oil for giving iodine by mouth.[15][14]

Cancer therapies

Poppyseed oil had long been used as a carrier for embolizing agents to treat tumors. In the 1980's, in order to better understand the action of these agents, poppyseed oil was replaced with lipiodol, to use its properties as a contrast agent.[16] It soon became apparent that the lipiodol was selectively taken up by tumors. Whether this is true also of poppyseed oil is unknown.

Iodized poppy-seed oil has an especially high rate of uptake into the cells of hepatocellular carcinoma (HCC). This property was soon recognized as an opportunity to deliver to HCC a variety of highly toxic chemotherapy and radiotherapy agents,[17] and formed the basis of several therapies for HCC not treatable by surgery alone.[18][19] Injected emulsions of epirubicin in lipiodol popular, but greater stability needed.[20] [21]

Lipiodol is under investigation as an adjuvant and carrier for use in chemotherapy to treat hepatocellular carcinoma (HCC). It increases the uptake and hence the cytotoxicity of doxorubicin in HCC cells[22] (and also in hepatoblastoma cells[23]). As a carrier, it is under investigation in conjunction with a lipophilic compound of platinum,[24] and in conjunction with a complex derivative of neocarzinostatin.[25] It also is being investigated as a radiation therapy against hepatocellular carcinoma, by being loaded with an isotope of iodine, iodine-131.[26]

Similarly, lipiodol has been used with the chemotherapy agent epirubicin, but with less success than with doxorubicin.[citation needed] Epirubicin is less lipophilic than doxorubicin. However, a "water/oil/water" microemulsion, in which epirubicin was dissolved in droplets of water, and the droplets were suspended in lipiodol, did significantly increase uptake of epirubicin by HCC cells.[27]

Lipiodol is often used in transarterial embolization (TAE), a treatment for HCC, with and without an additional chemotherapy agent. A systematic review of cohort and randomized studies found that TAE improves survival, but found no evidence of additional benefit for using either chemotherapy agents or lipiodol in TAE.[28]

History

Opium poppy seed pod

An early 20th century industry manual states that while the opium poppy was grown extensively in Eurasia, most of the world production of poppyseed oil occurred in France and Germany, from poppy seeds imported from other countries. From 1900 to 1911, France and Germany together produced on the order of 60,000,000 kilograms per year. At that time, poppyseed oil was used primarily to dress salads and frequently was adulterated with sesame oil and hazelnut oil to improve the taste of oil from stored (rancid) seeds. Poppyseed oil was used to adulterate olive oil and peach kernel oil.[1] Poor quality poppyseed oil was valuable in the soap industry.

Some pharmaceutical uses of the other major product of Papaver somniferum, opium, were recognized thousands of years ago. In contrast, pharmaceutical uses of poppyseed oil began in the 20th century. Iodized poppyseed oil was the subject of a 1959 article in a pharmaceutical research journal.[29] Various formulations were tried.[30] In 1976 a contrast agent for imaging the liver and spleen using computed tomography was proposed: AG 60.99, an emulsion of poppyseed oil.[31] A 1979 article reports on a new formulation, "improved" over ethiodol: "an emulsion of triglycerides of iodinated poppy seed oil".[32] After a series of experiments in animals, by 1981 iodized poppy seed oil was in use as a contrast agent for computed tomography in humans.[33]

See also

References

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Edible fats and oils
Fats Bacon fat · Blubber · Butter · Clarified butter · Cocoa butter · Dripping · Duck fat · Ghee · Lard · Margarine · Niter kibbeh · Salo · Schmaltz · Shea butter · Smen · Suet · Tallow · Vegetable shortening
Oils Almond oil · Argan oil · Avocado oil · Canola oil · Cashew oil · Castor oil · Coconut oil · Colza oil · Corn oil · Cottonseed oil · Fish oil · Grape seed oil · Hazelnut oil · Hemp oil · Linseed oil (flaxseed oil) · Macadamia oil · Marula oil · Mongongo nut oil · Mustard oil · Olive oil · Palm oil (palm kernel oil) · Peanut oil · Pecan oil · Perilla oil · Pine nut oil · Pistachio oil · Poppyseed oil · Pumpkin seed oil · Rapeseed oil · Rice bran oil · Safflower oil · Sesame oil · Soybean oil · Sunflower oil · Tea seed oil · Walnut oil · Watermelon seed oil
See also: List of vegetable oils · Cooking oil · Essential oil
Contrast media (V08)
X-ray
Iodinated, Water-soluble
Nephrotropic, high osmolar Diatrizoic acid# · Metrizoic acid · Iodamide · Iotalamic acid · Ioxitalamic acid · Ioglicic acid · Acetrizoic acid · Iocarmic acid · Methiodal · Diodone
Nephrotropic, low osmolar Metrizamide · Iohexol# · Ioxaglic acid · Iopamidol · Iopromide · Iotrolan · Ioversol · Iopentol · Iodixanol · Iomeprol · Iobitridol · Ioxilan
Hepatotropic Iodoxamic acid · Iotroxic acid · Ioglycamic acid · Adipiodone · Iobenzamic acid · Iopanoic acid · Iocetamic acid · Sodium iopodate · Tyropanoic acid · Calcium iopodate
Iodinated, Non-water-soluble Ethyl esters of iodised fatty acids · Iopydol · Propyliodone · Iofendylate · Lipiodol
Non-iodinated Barium sulfate#
MRI
Paramagnetic Gadopentetic acid · Gadoteric acid · Gadodiamide · Gadolinium · Gadoteridol · Mangafodipir · Gadoversetamide · Ferric ammonium citrate · Gadobenic acid · Gadobutrol · Gadoxetic acid
Superparamagnetic Ferumoxsil · Ferristene · Iron oxide, nanoparticles
Other Perflubron
Ultrasound Microspheres of human albumin · Microparticles of galactose · Perflenapent · Microspheres of phospholipids · Sulfur hexafluoride
#WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III

Categories: Crops | Poppy seeds | Cooking oils | Vegetable oils | Painting materials

 

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Fri, 23 Oct 2009 08:31:28 GM

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