Oenothera is a genus of about 125 species of annual, biennial and perennial herbaceous flowering plants, native to North and South America. It is the type genus of the family Onagraceae. Common names include evening-primrose, suncups, and sundrops. The species vary in size from small alpine plants 10 cm tall (e.g. O. acaulis from Chile), to vigorous lowland species growing to 3 m (e.g. O. stubbei from Mexico). The leaves form a basal rosette at ground level and spiral up to the flowering stems; the leaves are dentate or deeply lobed (pinnatifid). The flowers open in the evening, hence the name "evening-primrose", and are yellow in most species but white, purple, pink or red in a few. Most native California species are white. The fragrant evening-primrose Oenothera caespitosa, a California species, first blooms white but turns pink or light magenta. One of the most distinctive features of the flower is the stigma with four branches, forming an X shape. Pollination is by Lepidoptera (moths) and bees; like many members of the Onagraceae, however, the pollen grains are loosely held together by viscin threads (see photo below), meaning that only bees that are morphologically specialized to gather this pollen can effectively pollinate the flowers (it cannot be held effectively in a typical bee scopa). Furthermore, the flowers are open at a time when most bee species are inactive, so the bees which visit Oenothera are also compelled to be vespertine temporal specialists. The seeds ripen from late summer to fall. Oenothera species are used as food plants by the larvae of some Lepidoptera species including Schinia felicitata and Schinia florida, both of which feed exclusively on the genus, the former exclusively on O. deltoides. In the wild, evening-primrose acts as a primary colonizer, quickly appearing wherever a patch of bare, undisturbed ground may be found. This means that it tends to be found in poorer environments such as dunes, roadsides, railway embankments and wasteland. It often occurs as a casual, eventually being out-competed by other species. An evening-primrose cultivated in England An evening-primrose blossom opening in PennsylvaniaThe genus Oenothera may have originated in Mexico and Central America  from which it spread into North and South America and, with the advent of international travel, species are now found in most temperate regions. During the Pleistocene era a succession of ice ages swept down across North America, with intervening warm periods. This was repeated for four ice ages, with four separate waves of colonization, each hybridizing with the remnants of the previous waves  This generated a present-day group of species forming the subsection Euoenothera which is very rich in genetic diversity, spread right across the North American continent. These species are morphologically diverse and are largely interfertile and so the species boundaries have been a source of dispute amongst taxonomists. This pattern of repeated colonizations resulted in a unique genetic conformation in the Euoenotherae whereby the chromosomes at meiosis can form into circles of varying size, rather than complete chromosome pairing as in common meiosis. This is the result of several reciprocal translocations between chromosomes so that the pairing occurs only at the tips. This phenomenon has some apparently non-Mendelian genetic consequences. By combining this mode of chromosome segregation with a system of balanced-lethal genes, genetic recombination is prevented and the plants enjoy the vigour of heterosis. This resulted in the evolution of a large number of sympatric races over North America, east of the Rocky Mountains. Analysis of the cytology of these races and of artificial hybrids between them allowed a detailed understanding of the genetic and geographic evolution of the Euoenotherae. This whole subject was a major area of genetic research during the first half of the 20th century. Evening-primrose was originally assigned to the genus Onagra, which gave the family Onagraceae its name. Onagra (meaning "(food of) onager") was first used in botany in 1587, and in English in Philip Miller's 1754 Gardeners Dictionary: Abridged. Its modern name Oenothera was published by Carolus Linnaeus in his Systema Naturae. William Baird suggests that since oeno means "wine" in Greek it refers to the fact that the root of the edible Oenothera biennis was used as a wine flavor additive. An oil is a substance that is in a viscous liquid state ("oily") at ambient temperatures or slightly warmer, and is both hydrophobic (immiscible with water) and lipophilic (miscible with other oils, literally). This general definition includes compound classes with otherwise unrelated chemical structures, properties, and uses, including vegetable oils, petrochemical oils, and volatile essential oils. Oil is a nonpolar substance.