Poppyseed oil
Encyclopedia
Poppyseed oil is an edible oil from poppy seed
Poppy seed
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...

s (seed
Seed
A seed 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...

s of Papaver somniferum, the opium poppy
Opium poppy
Opium poppy, Papaver somniferum, 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 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. Like poppy seeds, poppyseed oil is highly palatable, high in vitamin E
Vitamin E
Vitamin E is used to refer to a group of fat-soluble compounds that include both tocopherols and tocotrienols. There are many different forms of vitamin E, of which γ-tocopherol is the most common in the North American diet. γ-Tocopherol can be found in corn oil, soybean oil, margarine and dressings...

, and has no narcotic
Narcotic
The term narcotic originally referred medically to any psychoactive compound with any sleep-inducing properties. In the United States of America it has since become associated with opioids, commonly morphine and heroin and their derivatives, such as hydrocodone. The term is, today, imprecisely...

 properties.

Chemistry

Poppy seeds are notable for being especially high in tocopherol
Tocopherol
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...

s other than vitamin E (alpha-tocopherol). Poppyseed oil from one source has been reported to contain 30.9 mg gamma-tocopherol per 100 g. It also contains alpha and gamma tocotrienol
Tocotrienol
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 . The slight difference between tocotrienols and tocopherols lie in the unsaturated side chain having three double bonds in its farnesyl isoprenoid...

s, but not others. Compared to other vegetable oils, poppyseed oil has a moderate amount of phytosterol
Phytosterol
Phytosterols, which encompass plant sterols and stanols, are steroid compounds similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond. Stanols are saturated sterols, having no double bonds in the sterol ring structure. More than...

s: higher than soybean oil
Soybean oil
Soybean oil is a vegetable oil extracted from the seeds of the soybean . It is one of the most widely consumed cooking oils. As a drying oil, processed soybean oil is also used as a base for printing inks and oil paints...

 and peanut oil
Peanut oil
Peanut oil is an organic material oil derived from peanuts, noted to have the aroma and taste of its parent legume....

, lower than safflower oil, sesame oil
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, Japanese, Korean, and to a lesser extent Southeast Asian cuisine.The oil from the nutrient rich seed is popular in alternative...

, wheat germ oil
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 - a 28 carbon long-chain saturated primary alcohol found in a number of different vegetable waxes. Octacosanol has been studied as an...

, corn oil
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. Corn oil is generally less expensive than most other types of vegetable oils. One bushel of corn...

, and rice bran oil
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 and its mild flavor, making it suitable for high-temperature cooking methods such as stir frying and deep frying...

. Sterol
Sterol
Sterols, also known as steroid alcohols, are a subgroup of the steroids and an important class of organic molecules. They occur naturally in plants, animals, and fungi, with the most familiar type of animal sterol being cholesterol...

s in poppyseed oil consist almost entirely of campesterol
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. Banana, pomegranate, pepper, coffee, grapefruit, cucumber, onion, oat, potato and lemon grass are few examples of common...

, stigmasterol
Stigmasterol
Stigmasterol is one of a group of plant sterols, or phytosterols, that include beta-sitosterol, campesterol, ergosterol , brassicasterol, delta-7-stigmasterol and delta-7-avenasterol, that are chemically similar to animal cholesterol...

, sitosterol and delta 5-avenasterol. Poppyseed oil is high in linoleic acid
Linoleic acid
Linoleic acid is an unsaturated n-6 fatty acid. It is a colorless liquid at room temperature. In physiological literature, it has a lipid number of 18:2...

. Although not generally higher than safflower oil, it can be as high as 74.5%. Other triglyceride
Triglyceride
A triglyceride is an ester derived from glycerol and three fatty acids. There are many triglycerides, depending on the oil source, some are highly unsaturated, some less so....

s present in notable quantities are oleic acid
Oleic acid
Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable fats. It has the formula CH37CH=CH7COOH. It is an odorless, colourless oil, although commercial samples may be yellowish. The trans isomer of oleic acid is called elaidic acid...

 and palmitic acid
Palmitic acid
Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants. Its molecular formula is CH314CO2H. As its name indicates, it is a major component of the oil from palm trees . Palmitate is a term for the salts and esters of...

.

It is less likely than some other oils to become rancid. It is more stable than safflower oil and linseed oil
Linseed oil
Linseed oil, also known as flaxseed 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...

.

Poppyseed oil is a carrier oil
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...

, having little or no odor and a pleasant taste. The primary aroma compound
Aroma compound
An aroma compound, also known as odorant, aroma, fragrance or flavor, is a chemical compound that has a smell or odor...

 responsible for its flavor is 2-pentylfuran; also present are the volatile compounds 1-pentanol
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 8 alcohols with this molecular formula . The ester formed from butanoic acid and 1-pentanol, pentyl butyrate, smells like apricot...

, 1-hexanal, 1-hexanol
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, 2-hexanol and 3-hexanol, exist, both of which...

, and caproic acid.

Uses

In the 19th century poppy seed oil was used as cooking oil
Cooking oil
Cooking oil is purified fat of plant origin, which is usually liquid at room temperature ....

, lamp oil, and varnish
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...

, and was used to make paints and soaps. Today, all of these uses continue, and
poppyseed oil has additional culinary and pharmaceutical uses. Particularly notable are its uses as a carrier for oil paint
Oil paint
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...

s and as a pharmaceutical grade carrier for medicinal iodine and drugs.

Poppyseed oil was sometimes added to olive and almond oils (see Adulterant
Adulterant
An adulterant is a chemical substance which should not be contained within other substances for legal or other reasons. 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...

). In industrialized countries its most important culinary use these days is as a salad or dipping oil.

Oil painting

Poppyseed oil is a drying oil
Drying oil
A drying oil is an oil that hardens to a tough, solid film after a period of exposure to air. The oil hardens through a chemical reaction in which the components crosslink by the action of oxygen . Drying oils are a key component of oil paint and some varnishes...

. In oil painting
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...

, 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.

Poppyseed oil has been used for painting for at least 1500 years—one of the oldest known oil paintings, found in caves of Afghanistan
Afghanistan
Afghanistan , officially the Islamic Republic of Afghanistan, is a landlocked country located in the centre of Asia, forming South Asia, Central Asia and the Middle East. With a population of about 29 million, it has an area of , making it the 42nd most populous and 41st largest nation in the world...

 and dated to AD 650, was likely drawn using poppyseed oil. It is most often found in white paints, and as a varnish. Painters prepared poppyseed oil by hand until the late 19th century, when oil paints became available prepared in tubes. While poppyseed oil does not leave the unwanted yellow tint for which linseed oil
Linseed oil
Linseed oil, also known as flaxseed 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.

Contrast agent

Iodized poppyseed oil (oil with iodine
Iodine
Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....

 added) has several kinds of pharmaceutical uses. The first of these uses was as a radiocontrast
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...

 agent used in medical radiology
Radiology
Radiology is a medical specialty that employs the use of imaging to both diagnose and treat disease visualized within the human body. Radiologists use an array of imaging technologies to diagnose or treat diseases...

. The origin of this use is attributed to Jean-Athanase Sicard
Jean-Athanase Sicard
Jean-Athanase Sicard was a French neurologist and radiologist who was born in Marseille.He studied medicine in Marseille and Paris, where he studied with Charles Emile Troisier , Édouard Brissaud , Henri-Alexandre Danlos , Fulgence Raymond and Georges-Fernand-Isidore Widal...

 and Jacques Forestier
Jacques Forestier
Jacques Forestier was a French internist who was a pioneer in the field of rheumatology. He studied and practiced medicine in Paris, and was founder of the National French Society of Rheumatology...

. Two brand name formulations are ethiodol and lipiodol
Lipiodol
Lipiodol also known as ethiodized oil is a poppyseed oil used by injection as a radio-opaque contrast agent that is used to outline structures in radiological investigations. It is used in chemoembolization applications as a contrast agent in follow-up imaging. Lipiodol is also used in...

. 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 is not available, iodized poppyseed oil is the standard for preventing iodine deficiency
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 inlandareas where no marine foods are eaten—iodine deficiency gives rise to...

 and its complications including goiter. It may be given by mouth or by injection, injection being markedly more effective. The origin of this use is attributed to Paulo Campos
Paulo Campos
Paulo C. Campos was a Filipino physician and educator noted for his promotion of wider community health care and his achievements in the field of nuclear medicine for which he was dubbed as "The Father of Nuclear Medicine in the Philippines"...

. Usually it is given to adults and children by intramuscular injection
Intramuscular injection
Intramuscular injection is the injection of a substance directly into a muscle. In medicine, it is one of several alternative methods for the administration of medications . It is used for particular forms of medication that are administered in small amounts...

, 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
Polio vaccine
Two polio vaccines are used throughout the world to combat poliomyelitis . The first was developed by Jonas Salk and first tested in 1952. Announced to the world by Salk on April 12, 1955, it consists of an injected dose of inactivated poliovirus. An oral vaccine was developed by Albert Sabin...

 had good results. A randomized, double-blind, fully controlled trial in which lipiodol was given by mouth to children had disappointing results. A recent clinical trial
Clinical trial
Clinical trials are a set of procedures in medical research and drug development that are conducted to allow safety and efficacy data to be collected for health interventions...

 in which iodized oil was given by mouth found that the amount of iodine taken up (see bioavailability
Bioavailability
In pharmacology, bioavailability is a subcategory of absorption and is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. By definition, when a medication is administered...

) varied with the amount of oleic acid
Oleic acid
Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable fats. It has the formula CH37CH=CH7COOH. It is an odorless, colourless oil, although commercial samples may be yellowish. The trans isomer of oleic acid is called elaidic acid...

 in the oil. Poppyseed oil has relatively little oleic acid. Peanut oil
Peanut oil
Peanut oil is an organic material oil derived from peanuts, noted to have the aroma and taste of its parent legume....

 and rapeseed oil have far more oleic acid and are less expensive, and may be superior to poppyseed oil for giving iodine by mouth.

Cancer therapies

Poppyseed oil had long been used as a carrier for embolizing
Embolism
In medicine, an embolism is the event of lodging of an embolus into a narrow capillary vessel of an arterial bed which causes a blockage in a distant part of the body.Embolization is...

 agents to treat tumor
Tumor
A tumor or tumour is commonly used as a synonym for a neoplasm that appears enlarged in size. Tumor is not synonymous with cancer...

s. In the 1980s, in order to better understand the action of these agents, poppyseed oil was replaced with lipiodol, to use its properties as a contrast agent. 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, and formed the basis of several therapies for HCC not treatable by surgery alone. Injected emulsion
Emulsion
An emulsion is a mixture of two or more liquids that are normally immiscible . Emulsions are part of a more general class of two-phase systems of matter called colloids. Although the terms colloid and emulsion are sometimes used interchangeably, emulsion is used when both the dispersed and the...

s of epirubicin in lipiodol are popular, but greater stability is needed.
Lipiodol is under investigation as an adjuvant and carrier for use in chemotherapy
Chemotherapy
Chemotherapy is the treatment of cancer with an antineoplastic drug or with a combination of such drugs into a standardized treatment regimen....

 to treat hepatocellular carcinoma
Hepatocellular carcinoma
Hepatocellular carcinoma is the most common type of liver cancer. Most cases of HCC are secondary to either a viral hepatitide infection or cirrhosis .Compared to other cancers, HCC is quite a rare tumor in the United States...

 (HCC). It increases the uptake and hence the cytotoxicity of doxorubicin
Doxorubicin
Doxorubicin INN is a drug used in cancer chemotherapy. It is an anthracycline antibiotic, closely related to the natural product daunomycin, and like all anthracyclines, it works by intercalating DNA....

 in HCC cells (and also in hepatoblastoma
Hepatoblastoma
Hepatoblastoma is an uncommon malignant liver neoplasm occurring in infants and children and composed of tissue resembling fetal or mature liver cells or bile ducts. Affecting 1 in 1.5 million. They are usually present with an abdominal mass...

 cells). As a carrier, it is under investigation in conjunction with a lipophilic
Lipophilic
Lipophilicity, , refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. These non-polar solvents are themselves lipophilic — the axiom that like dissolves like generally holds true...

 compound of platinum
Platinum
Platinum is a chemical element with the chemical symbol Pt and an atomic number of 78. Its name is derived from the Spanish term platina del Pinto, which is literally translated into "little silver of the Pinto River." It is a dense, malleable, ductile, precious, gray-white transition metal...

, and in conjunction with a complex derivative of neocarzinostatin
Neocarzinostatin
Neocarzinostatin is a macromolecular chromoprotein enediyne antibiotic with anti-tumoral activity secreted by Streptomyces macromomyceticus....

. It also is being investigated as a radiation therapy
Radiation therapy
Radiation therapy , radiation oncology, or radiotherapy , sometimes abbreviated to XRT or DXT, is the medical use of ionizing radiation, generally as part of cancer treatment to control malignant cells.Radiation therapy is commonly applied to the cancerous tumor because of its ability to control...

 against hepatocellular carcinoma, by being loaded with an isotope of iodine, iodine-131
Iodine-131
Iodine-131 , also called radioiodine , is an important radioisotope of iodine. It has a radioactive decay half-life of about eight days. Its uses are mostly medical and pharmaceutical...

.

Similarly, lipiodol has been used with the chemotherapy agent epirubicin
Epirubicin
Epirubicin is an anthracycline drug used for chemotherapy. It is marketed by Pfizer under the trade name Ellence in the US and Pharmorubicin or Epirubicin Ebewe elsewhere....

, but with less success than with doxorubicin. Epirubicin is less lipophilic than doxorubicin. However, a "water/oil/water" microemulsion
Microemulsion
Microemulsions are clear, thermodynamically stable, isotropic liquid mixtures of oil, water and surfactant, frequently in combination with a cosurfactant. The aqueous phase may contain salt and/or other ingredients, and the "oil" may actually be a complex mixture of different hydrocarbons and olefins...

, in which epirubicin was dissolved in droplets of water, and the droplets were suspended in lipiodol, significantly increased uptake of epirubicin by HCC cells.

Lipiodol is often used in transarterial embolization (TAE), a treatment for HCC, with and without an additional chemotherapy agent. A systematic review
Systematic review
A systematic review is a literature review focused on a research question that tries to identify, appraise, select and synthesize all high quality research evidence relevant to that question. Systematic reviews of high-quality randomized controlled trials are crucial to evidence-based medicine...

 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.

History

An early 20th century industry manual states that while the opium poppy was grown extensively in Eurasia
Eurasia
Eurasia is a continent or supercontinent comprising the traditional continents of Europe and Asia ; covering about 52,990,000 km2 or about 10.6% of the Earth's surface located primarily in the eastern and northern hemispheres...

, 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
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, Japanese, Korean, and to a lesser extent Southeast Asian cuisine.The oil from the nutrient rich seed is popular in alternative...

 and hazelnut oil to improve the taste of oil from stored (rancid) seeds. Poppyseed oil was used to adulterate olive oil
Olive oil
Olive oil is an oil obtained from the olive , a traditional tree crop of the Mediterranean Basin. It is commonly used in cooking, cosmetics, pharmaceuticals, and soaps and as a fuel for traditional oil lamps...

 and peach kernel oil. Poor quality poppyseed oil was valuable in the soap industry.

Some pharmaceutical uses of the other major product of Papaver somniferum, opium
Opium
Opium is the dried latex obtained from the opium poppy . Opium contains up to 12% morphine, an alkaloid, which is frequently processed chemically to produce heroin for the illegal drug trade. The latex also includes codeine and non-narcotic alkaloids such as papaverine, thebaine and noscapine...

, 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. Various formulations were tried. In 1976 a contrast agent for imaging the liver
Liver
The liver is a vital organ present in vertebrates and some other animals. It has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...

 and spleen
Spleen
The spleen is an organ found in virtually all vertebrate animals with important roles in regard to red blood cells and the immune system. In humans, it is located in the left upper quadrant of the abdomen. It removes old red blood cells and holds a reserve of blood in case of hemorrhagic shock...

 using computed tomography
Computed tomography
X-ray computed tomography or Computer tomography , is a medical imaging method employing tomography created by computer processing...

 was proposed: AG 60.99, an emulsion of poppyseed oil. A 1979 article reports on a new formulation, "improved" over ethiodol: "an emulsion of triglycerides of iodinated poppy seed oil". After a series of experiments in animals, by 1981 iodized poppy seed oil was in use as a contrast agent for computed tomography
Computed tomography
X-ray computed tomography or Computer tomography , is a medical imaging method employing tomography created by computer processing...

in humans.
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