Heneicosane

Last updated
Heneicosane
Heneicosane.svg
Names
Preferred IUPAC name
Henicosane
Other names
n-Heneicosane
Identifiers
3D model (JSmol)
1748500
ChEBI
ECHA InfoCard 100.010.109 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-118-9
PubChem CID
UNII
  • InChI=1S/C21H44/c1-3-5-7-9-11-13-15-17-19-21-20-18-16-14-12-10-8-6-4-2/h3-21H2,1-2H3 Yes check.svgY
    Key: FNAZRRHPUDJQCJ-UHFFFAOYSA-N Yes check.svgY
  • CCCCCCCCCCCCCCCCCCCCC
Properties
C21H44
Molar mass 296.583 g·mol−1
AppearanceWaxy solid
Density 0.7919 g mL−1
Melting point 40.5 °C (104.9 °F; 313.6 K)
Boiling point 356.10 °C; 672.98 °F; 629.25 K
2.9×10−11 g/L
log P 10.65
Vapor pressure 8.73X10-5 mm Hg
120 atm•m3/mole
1.4441
Hazards
NFPA 704 (fire diamond)
1
1
0
Flash point 113 °C (235 °F; 386 K)
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Heneicosane is the organic compound with the formula CH3(CH2)19CH3. It is the straight chain, saturated C21 hydrocarbon. It is a white wax.

Natural occurrence

Heneicosane is used as a pheromone by the queen or king termites in the species Reticulitermes flavipes . [1] It also attracts mosquitoes in the genus Aedes and can be used in mosquito baits. [2] This works in nature as the hydrocarbon is produced in the skin of the larva. A 1:100000 fraction in water is the most attractive, but if the concentration is 1:1000 then mosquitoes are repelled instead. [3] Heneicosane is one of the major components of the safflower flower essential oil ( Carthamus tinctorius ). [4] All parts of the plant Periploca laevigata contain heneicosane. [5] Rosa damascena flower essential oil contains 5% heneicosane. [6] Sambucus nigra contains 2.3%.

Related Research Articles

Mosquito Family of flies

Mosquitoes are members of a group of almost 3,600 species of small flies within the family Culicidae. The word "mosquito" is Spanish and Portuguese for "little fly". Mosquitoes have a slender segmented body, one pair of wings, one pair of halteres, three pairs of long hair-like legs, and elongated mouthparts.

Termite Social insects related to cockroaches

Termites are eusocial insects that are classified at the taxonomic rank of infraorder Isoptera, or alternatively as epifamily Termitoidae, within the order Blattodea. Termites were once classified in a separate order from cockroaches, but recent phylogenetic studies indicate that they evolved from cockroaches, as they are deeply nested within the group, and the sister group to wood eating cockroaches of the genus Cryptocercus. Previous estimates suggested the divergence took place during the Jurassic or Triassic. More recent estimates suggest that they have an origin during the Late Jurassic, with the first fossil records in the Early Cretaceous. About 3,106 species are currently described, with a few hundred more left to be described. Although these insects are often called "white ants", they are not ants, and are not closely related to ants.

Terpene Class of oily organic compounds found in plants

Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes are further classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), etc. A well known monoterpene is alpha-pinene, a major component of turpentine.

Essential oil Hydrophobic liquid containing volatile aroma compounds from plants

An essential oil is a concentrated hydrophobic liquid containing volatile chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the oil of the plant from which they were extracted, such as oil of clove. An essential oil is essential in the sense that it contains the essence of the plant's fragrance—the characteristic fragrance of the plant from which it is derived. The term "essential" used here does not mean indispensable or usable by the human body, as with the terms essential amino acid or essential fatty acid, which are so called because they are nutritionally required by a living organism.

Patchouli Species of flowering plant

Patchouli is a species of flowering plant in the family Lamiaceae, commonly called the mint or deadnettle family. The plant grows as a bushy perennial herb, with erect stems reaching up to 75 centimetres (2.5 ft) in height and bearing small, pale pink-white flowers.

<i>Aedes albopictus</i> Species of fly

Aedes albopictus, from the mosquito (Culicidae) family, also known as the (Asian) tiger mosquito or forest mosquito, is a mosquito native to the tropical and subtropical areas of Southeast Asia. In the past few centuries, however, this species has spread to many countries through the transport of goods and international travel. It is characterized by the white bands on its legs and body.

Safflower Species of plant

Safflower, Carthamus tinctorius, is a highly branched, herbaceous, thistle-like annual plant in the sunflower family Asteraceae. It is commercially cultivated for vegetable oil extracted from the seeds and was used by the early Spanish colonies along the Rio Grande as a substitute for saffron. Plants are 30 to 150 cm tall with globular flower heads having yellow, orange, or red flowers. Each branch will usually have from one to five flower heads containing 15 to 20 seeds per head. Safflower is native to arid environments having seasonal rain. It grows a deep taproot which enables it to thrive in such environments.

gamma-Linolenic acid or GLA is a fatty acid found primarily in seed oils. When acting on GLA, arachidonate 5-lipoxygenase produces no leukotrienes and the conversion by the enzyme of arachidonic acid to leukotrienes is inhibited.

Absolute (perfumery)

Used in perfumery and aromatherapy, absolutes are similar to essential oils. They are concentrated, highly aromatic, oily mixtures extracted from plants. Whereas essential oils are produced by distillation, boiling or pressing, absolutes are produced through solvent extraction, or more traditionally, through enfleurage.

<i>Chrysopogon zizanioides</i> Species of plant

Chrysopogon zizanioides, commonly known as vetiver and khus, is a perennial bunchgrass of the family Poaceae.

Yarrow oil

Yarrow essential oil is a volatile oil including the chemical proazulene. The dark blue essential oil is extracted by steam distillation of the flowers of yarrow.

Insect repellent Substance which repels insects

An insect repellent is a substance applied to skin, clothing, or other surfaces to discourage insects from landing or climbing on that surface. Insect repellents help prevent and control the outbreak of insect-borne diseases such as malaria, Lyme disease, dengue fever, bubonic plague, river blindness, and West Nile fever. Pest animals commonly serving as vectors for disease include insects such as flea, fly, and mosquito; and ticks (arachnids).

Nonacosane is a straight-chain hydrocarbon with a molecular formula of C29H60, and the structural formula CH3(CH2)27CH3. It has 1,590,507,121 constitutional isomers.

Rose oil Essential oil

Rose oil is the essential oil extracted from the petals of various types of rose. Rose ottos are extracted through steam distillation, while rose absolutes are obtained through solvent extraction, the absolute being used more commonly in perfumery. The production technique originated in Persia. Even with their high price and the advent of organic synthesis, rose oils are still perhaps the most widely used essential oil in perfumery.

<i>p</i>-Cresol Chemical compound

para-Cresol, also 4-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of o-cresol and m-cresol.

Farnesene Chemical compound

The term farnesene refers to a set of six closely related chemical compounds which all are sesquiterpenes. α-Farnesene and β-farnesene are isomers, differing by the location of one double bond. α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene and β-farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. The alpha form can exist as four stereoisomers that differ about the geometry of two of its three internal double bonds. The beta isomer exists as two stereoisomers about the geometry of its central double bond.

<i>Rosa <span style="font-style:normal;">×</span> damascena</i> Species of plant in the genus Rosa

Rosa × damascena, more commonly known as the Damask rose, or sometimes as Bulgarian rose, Turkish rose, Taif rose, Arab rose, Ispahan rose and Castile rose, is a rose hybrid, derived from Rosa gallica and Rosa moschata. DNA analysis has shown that a third species, Rosa fedtschenkoana, has made some genetic contributions to the Damask rose.

Catnip Nepeta cataria; species of plant

Nepeta cataria, commonly known as catnip, catswort, catwort, and catmint, is a species of the genus Nepeta in the family Lamiaceae, native to southern and eastern Europe, the Middle East, Central Asia, and parts of China. It is widely naturalized in northern Europe, New Zealand, and North America. The common name catmint can also refer to the genus as a whole.

<i>Carapa guianensis</i> Species of tree

Carapa guianensis is a species of tree in the family Meliaceae, also known by the common names andiroba or crabwood.

Aedes taeniorhynchus, or the black salt marsh mosquito, is a mosquito in the family Culicidae. It is a carrier for encephalitic viruses including Venezuelan equine encephalitis and can transmit Dirofilaria immitis. It resides in the Americas and is known to bite mammals, reptiles, and birds. Like other mosquitoes, Ae. taeniorhynchus adults survive on a combination diet of blood and sugar, with females generally requiring a blood meal before laying eggs.

References

  1. "Termite queen, king recognition pheromone identified". 19 March 2018. Retrieved 21 March 2018.
  2. Kumar, P; Lomash, V; Jatav, PC; Kumar, A; Pant, SC (January 2016). "Prenatal developmental toxicity study of n-heneicosane in Wistar rats". Toxicology and Industrial Health. 32 (1): 118–25. doi:10.1177/0748233713498438. PMID   24060842. S2CID   206543815.
  3. Seenivasagan, T; Sharma, KR; Sekhar, K; Ganesan, K; Prakash, S; Vijayaraghavan, R (March 2009). "Electroantennogram, flight orientation, and oviposition responses of Aedes aegypti to the oviposition pheromone n-heneicosane". Parasitology Research. 104 (4): 827–33. doi:10.1007/s00436-008-1263-2. PMID   19018567. S2CID   6880282.
  4. Asgarpanah, J; Kazemivash, N (February 2013). "Phytochemistry, pharmacology and medicinal properties of Carthamus tinctorius L.". Chinese Journal of Integrative Medicine . 19 (2): 153–9. doi:10.1007/s11655-013-1354-5. PMID   23371463. S2CID   386921.
  5. Zito, P; Sajeva, M; Bruno, M; Rosselli, S; Maggio, A; Senatore, F (2013). "Essential oils composition of Periploca laevigata Aiton subsp. angustifolia (Labill.) Markgraf (Apocynaceae-Periplocoideae)". Natural Product Research. 27 (3): 255–65. doi:10.1080/14786419.2012.671319. PMID   22439883. S2CID   205838364.
  6. Sadraei, H; Asghari, G; Emami, S (January 2013). "Inhibitory effect of Rosa damascena Mill flower essential oil, geraniol and citronellol on rat ileum contraction". Research in Pharmaceutical Sciences. 8 (1): 17–23. PMC   3895296 . PMID   24459472.