Isoprene

Isoprene

Names
IUPAC name 2-methyl-1,3-butadiene
Other names terpene
Identifiers
CAS Number	78-79-5 Y
3D model (JSmol)	Interactive image
ECHA InfoCard	100.001.040
KEGG	C16521 N
CompTox Dashboard (EPA)	DTXSID2020761
SMILES C=C(C)C=C
Properties
Chemical formula	C5H8
Molar mass	68.12 g/mol
Density	0.681 g/cm³
Melting point	−143.95 °C
Boiling point	34.067 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Isoprene (short for isoterpene), or 2-methyl-1,3-butadiene, is a common organic compound with the formula CH₂=C(CH₃)CH=CH₂. Under standard conditions it is a colorless liquid. However, this compound is highly volatile because of its low boiling point.

Isoprene (C₅H₈) is the monomer of natural rubber and also a common structure motif to an immense variety of other naturally occurring compounds, collectively termed the isoprenoids. Molecular formula of isoprenoids are multiples of isoprene in the form of (C₅H₈)_n, and this is termed the isoprene rule. The functional isoprene units in biological systems are dimethylallyl diphosphate (DMADP) and its isomer isopentenyl diphosphate (IDP).

The singular terms “isoprene” and “terpene” are synonymous whereas the plurals “isoprenes” or “terpenes” refer to terpenoids (isoprenoids).

Isoprene is produced and emitted by many species of trees into the atmosphere (major producers are oaks, poplars, eucalyptus and some legumes). The yearly production of isoprene emissions by vegetation is around 600 Tg, with half that coming from tropical broadleaf trees and the remainder coming from shrubs.^[1] This is about equivalent to methane emission into the atmosphere and accounts for ~1/3 of all hydrocarbons released into the atmosphere. After release, isoprene is converted by free radicals (like the hydroxyl (OH) radical) and to a lesser extent by ozone ^[2] into various species, such as aldehydes, hydroperoxides, organic nitrates and epoxides, which mix into water droplets and help create aerosols and haze.^[3][4] While most in the field acknowledges isoprene emission effect aerosol formation, whether isoprene increases or decreases aerosol formation is debated. A second major effect of isoprene on the atmosphere is that in presence of nitric oxides (NO_x) it contributes to the formation of tropospheric (lower atmosphere) ozone, which is one of the leading air pollutants in many countries. Isoprene itself is normally not regarded as a pollutant, as it is one of the natural products from plants. Formation of tropospheric ozone is only possible in presence of high levels of NO_x, which comes almost exclusively from industrial activities. In fact, isoprene can have the opposite effect and quench ozone formation under low levels of NO_x.

Isoprene is made through the methyl-erythritol 4-phosphate pathway (MEP pathway, also called the non-mevalonate pathway) in the chloroplasts of plants. One of the two end products of MEP pathway, dimethylallyl diphosphate (DMADP), is catalyzed by the enzyme isoprene synthase to form isoprene. Therefore, inhibitors that block the MEP pathway, such as fosmidomycin, also blocks isoprene formation. Isoprene emission increases dramatically with temperature and maximizes at around 40 °C. This has led to the hypothesis that isoprene may protect plants against heat stress (thermotolerance hypothesis, see below). Emission of isoprene is also observed in some bacteria and this is thought to come from non-enzymatic degradations from DMADP.

Isoprene emission in plants is controlled both by the availability of substrate (DMADP) and by enzyme (isoprene synthase) activity. In particular, light, CO₂ and O₂ dependencies of isoprene emission are controlled by substrate availability, whereas temperature dependency of isoprene emission is regulated both by substrate level and enzyme activity.

Isoprene emission appears to be a mechanism that trees use to combat abiotic stresses.^[5] In particular, isoprene has been shown to protect against moderate heat stresses (~ 40 °C). It was proposed that isoprene emission was specifically used by plants to protect against large fluctations in leaf temperature.

Isoprene is incorporated into and helps stabilize cell membranes in response to heat stress, conferring some tolerance to heat spikes. Isoprene may also confer some resistance to reactive oxygen species.^[5] The amount of isoprene released from isoprene-emitting vegetation depends on leaf mass, leaf area, light (particularly photosynthetic photon flux density, or PPFD), and leaf temperature. Thus, during the night, little isoprene is emitted from tree leaves, whereas daytime emissions are expected to be substantial during hot and sunny days, up to 25 μg/(g dry-leaf-weight)/hour in many oak species ^[6]

In general, it is the most common hydrocarbon found in the human body^[7], ^[8]. The estimated production rate of isoprene in the human body is 0.15 µmol/(kg·h), equivalent to approximately 17 mg/day for a person weighing 70 kg. Isoprene is also common in low concentrations in many foods.

Isoprene was first isolated by thermal decomposition of natural rubber.^[9] It is most readily available industrially as a byproduct of the thermal cracking of naphtha or oil, as a side product in the production of ethylene. About 800,000 tonnes are produced annually. About 95% of isoprene production is used to produce cis-1,4-polyisoprene—a synthetic version of natural rubber.

Natural rubber is a polymer of isoprene—most often cis-1,4-polyisoprene—with a molecular weight of 100,000 to 1,000,000. Typically, a few percent of other materials, such as proteins, fatty acids, resins, and inorganic materials are found in high-quality natural rubber. Some natural rubber sources called gutta percha are composed of trans-1,4-polyisoprene, a structural isomer that has similar, but not identical, properties.^[10]

Isoprene is a common structural motif in biological systems. The isoprenoids (for example, the carotenes are tetraterpenes) are derived from isoprene. Also derived from isoprene are phytol, retinol (vitamin A), tocopherol (vitamin E), dolichols, and squalene. Heme A has an isoprenoid tail, and lanosterol, the sterol precursor in animals, is derived from squalene and hence from isoprene. The functional isoprene units in biological systems are dimethylallyl diphosphate (DMADP) and its isomer isopentenyl diphosphate (IDP), which are used in the biosynthesis of naturally occurring isoprenoids such as carotenoids, quinones, lanosterol derivatives (e.g. steroids) and the prenyl chains of certain compounds (e.g. phytol chain of chlorophyll).

• Merck Index: an encyclopedia of chemicals, drugs, and biologicals, Susan Budavari (ed.), 11th Edition, Rahway, NJ : Merck, 1989, ISBN 0-911910-28-X
• Poisson, N. (2000). "Impact of nonmethanehydrocarbons on tropospheric chemistry and the oxidizing power of the global troposphere: 3-dimensional modelling results". Journal of Atmospheric Chemistry. 36 (2): 157–230. doi:10.1023/A:1006300616544. ISSN 0167-7764. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
• Claeys, M. (2004). "Formation of secondary organic aerosols through photooxidation of isoprene". Science. 303 (5661): 1173–1176. doi:10.1126/science.1092805. ISSN 0036-8075. PMID 14976309. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
• Pier, P. A. (1997). "Seasonal isoprene emission rates and model comparisons using whole-tree emissions from white oak". Journal of Geophysical Research. 102 (D20): 23, 963–23, 971. Bibcode:1997JGR...10223963P. doi:10.1029/96JD03786. ISSN 0148-0227. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
• Poschl, U. (2000). "Development and intercomparison of condensed isoprene oxidation mechanisms for global atmospheric modeling". Journal of Atmospheric Chemistry. 37 (1): 29–52. doi:10.1023/A:1006391009798. ISSN 0167-7764. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
• Monson, R. K. (2001). "Biospheric trace gas fluxes and their control over tropospheric chemistry". Annual Review of Ecology and Systematics. 32: 547–576. doi:10.1146/annurev.ecolsys.32.081501.114136. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

• Report on Carcinogens, Eleventh Edition; U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program
• Science News article describing how isoprene released by plants is converted to light-scattering aerosols