Prenol

Last updated
Prenol
Prenol structure.png
Prenol-3D-balls.png
Names
Preferred IUPAC name
3-Methylbut-2-en-1-ol
Other names
3,3-Dimethylallyl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.312 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-141-4
PubChem CID
UNII
  • InChI=1S/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3 Yes check.svgY
    Key: ASUAYTHWZCLXAN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3
  • OC\C=C(/C)C
Properties [1]
C5H10O
Molar mass 86.132 g/mol
Density 0.848 g/cm3
Melting point −59 °C (−74 °F; 214 K) (calculated)
Boiling point 142 °C (288 °F; 415 K) (approximation)
17 g/100 ml (20 °C)
log P 0.91
Vapor pressure 3.17 hPa (25 °C, extrapolated)
Hazards [1] [2]
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H226, H302
P210, P233, P240, P241, P242, P243, P264, P270, P301+P312, P303+P361+P353, P330, P370+P378, P403+P235, P501
Flash point 43.3 °C (109.9 °F; 316.4 K) [note 1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Prenol, or 3-methyl-2-buten-1-ol, is a natural alcohol. It is one of the most simple terpenoids. It is a clear colorless oil that is reasonably soluble in water and miscible with most common organic solvents. It has a fruity odor and is used occasionally in perfumery.

Contents

Prenol occurs naturally in citrus fruits, cranberry, bilberry, currants, grapes, raspberry, blackberry, tomato, white bread, hop oil, coffee, arctic bramble, cloudberry and passion fruit. [1] It is also manufactured industrially by BASF (in Ludwigshafen, Germany) and by Kuraray (in Asia) as an intermediate to pharmaceuticals and aroma compounds. Global production in 2001 was between 6000 and 13,000 tons. [1]

Industrial production

Prenol is produced industrially by the reaction of formaldehyde with isobutene, followed by the isomerization of the resulting isoprenol (3-methyl-3-buten-1-ol). [1] [3]

The reaction of isobutene with formaldehyde to give isoprenol, the first step in the industrial manufacture of prenol Isoprenol prepn.png
The reaction of isobutene with formaldehyde to give isoprenol, the first step in the industrial manufacture of prenol
The isomerization of isoprenol to prenol, the second step in the industrial manufacture of prenol Prenol prepn.png
The isomerization of isoprenol to prenol, the second step in the industrial manufacture of prenol

Uses

Prenol is mainly used as a precursor to citral, an intermediate in the industrial production of vitamin A, E, and K. For this purpose, prenol is oxidized to the aldehyde prenal. [4]

Polyprenols

Prenol is a building block of isoprenoid alcohols, which have the general formula:

H–[CH2CCH3=CHCH2]n–OH

The repeating C5H8 moiety in the brackets is called isoprene, and these compounds are sometimes called 'isoprenols'. [5] They should not be confused with isoprenol, which is an isomer of prenol with a terminal double bond. The simplest isoprenoid alcohol is geraniol (n = 2): higher oligomers include farnesol (n = 3) and geranylgeraniol (n = 4).

When the isoprene unit attached to the alcohol is saturated, the compound is referred to as a dolichol. Dolichols are important as glycosyl carriers in the synthesis of polysaccharides. They also play a major role in protecting cellular membranes, stabilising cell proteins and supporting the body's immune system.

Prenol is polymerized by dehydration reactions; when there are at least five isoprene units (n in the above formula is greater than or equal to five), the polymer is called a polyprenol. Polyprenols can contain up to 100 isoprene units (n = 100) linked end to end with the hydroxyl group (–OH) remaining at the end. These long-chain isoprenoid alcohols are also called ‘terpenols’. They are important in the acylation of proteins, carotenoids, and fat-soluble vitamins A, E and K.

Polyprenols also play a vital role in cell metabolism. Research indicates that ingested polyprenols are metabolised by human and animal liver into dolichols which then take part in the dolichol phosphate cycle and are therefore easily assimilated by humans and animals. The pharmacological activity of polyprenols is based on their substitutive effect in the case of dolichol deficits which are observed with chronic inflammatory, degenerative and oncological diseases. [6]

Live conifer needles are one of the richest and most widely available sources for polyprenol extraction in the world. Commercial extraction of polyprenols involves a soft extraction procedure that enables them to be extracted without destroying their biological activity. [7]

Notes

  1. BASF gives a value for the flash point of prenol of 51.5 °C (125 °F), which is used in the OECD Screening Information Data Set (SIDS): the difference in the two values does not alter the safety classification of prenol as a category 3 flammable liquid (GHS) or class II combustible liquid (U.S., 29 C.F.R § 1910.106, NFPA class F2).

Related Research Articles

<span class="mw-page-title-main">Carotene</span> Class of compounds

The term carotene (also carotin, from the Latin carota, "carrot") is used for many related unsaturated hydrocarbon substances having the formula C40Hx, which are synthesized by plants but in general cannot be made by animals (with the exception of some aphids and spider mites which acquired the synthesizing genes from fungi). Carotenes are photosynthetic pigments important for photosynthesis. Carotenes contain no oxygen atoms. They absorb ultraviolet, violet, and blue light and scatter orange or red light, and (in low concentrations) yellow light.

<span class="mw-page-title-main">Lipid</span> Substance of biological origin that is soluble in nonpolar solvents

Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins, monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology.

Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. It is produced by many plants and animals (including humans) and its polymers are the main component of natural rubber.

The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.

<span class="mw-page-title-main">Terpene</span> Class of oily organic compounds found in plants

Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.

<span class="mw-page-title-main">1,4-Butanediol</span> One of four stable isomers of butanediol

1,4-Butanediol, also called Butane-1,4-diol (other names include 1,4-B, BD, BDO and 1,4-BD), is a primary alcohol and an organic compound with the formula HOCH2CH2CH2CH2OH. It is a colorless viscous liquid first synthesized in 1890 via acidic hydrolysis of N,N'-dinitro-1,4-butanediamine by Dutch chemist Pieter Johannes Dekkers, who called it "tetramethylene glycol".

<span class="mw-page-title-main">Prenylation</span> Addition of hydrophobic moieties to proteins or other biomolecules

Prenylation is the addition of hydrophobic molecules to a protein or a biomolecule. It is usually assumed that prenyl groups (3-methylbut-2-en-1-yl) facilitate attachment to cell membranes, similar to lipid anchors like the GPI anchor, though direct evidence of this has not been observed. Prenyl groups have been shown to be important for protein–protein binding through specialized prenyl-binding domains.

Dolichol refers to any of a group of long-chain mostly unsaturated organic compounds that are made up of varying numbers of isoprene units terminating in an α-saturated isoprenoid group, containing an alcohol functional group.

<span class="mw-page-title-main">Methyl isobutyl ketone</span> Chemical compound

Methyl isobutyl ketone (MIBK, 4-methylpentan-2-one) is an organic compound with the condensed chemical formula (CH3)2CHCH2C(O)CH3. This ketone is a colourless liquid that is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

<span class="mw-page-title-main">Liquid–liquid extraction</span> Method to separate compounds or metal complexes

Liquid–liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds or metal complexes, based on their relative solubilities in two different immiscible liquids, usually water (polar) and an organic solvent (non-polar). There is a net transfer of one or more species from one liquid into another liquid phase, generally from aqueous to organic. The transfer is driven by chemical potential, i.e. once the transfer is complete, the overall system of chemical components that make up the solutes and the solvents are in a more stable configuration. The solvent that is enriched in solute(s) is called extract. The feed solution that is depleted in solute(s) is called the raffinate. Liquid–liquid extraction is a basic technique in chemical laboratories, where it is performed using a variety of apparatus, from separatory funnels to countercurrent distribution equipment called as mixer settlers. This type of process is commonly performed after a chemical reaction as part of the work-up, often including an acidic work-up.

<span class="mw-page-title-main">Isopentenyl pyrophosphate</span> Chemical compound

Isopentenyl pyrophosphate is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway and in the non-mevalonate MEP pathway of isoprenoid precursor biosynthesis. Isoprenoid precursors such as IPP, and its isomer DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids.

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

<span class="mw-page-title-main">Crotonaldehyde</span> Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

The non-mevalonate pathway—also appearing as the mevalonate-independent pathway and the 2-C-methyl-D-erythritol 4-phosphate/1-deoxy-D-xylulose 5-phosphate (MEP/DOXP) pathway—is an alternative metabolic pathway for the biosynthesis of the isoprenoid precursors isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). The currently preferred name for this pathway is the MEP pathway, since MEP is the first committed metabolite on the route to IPP.

<span class="mw-page-title-main">3-Methylpyridine</span> Chemical compound

3-Methylpyridine or 3-picoline, is an organic compound with formula 3-CH3C5H4N. It is one of three positional isomers of methylpyridine, whose structures vary according to where the methyl group is attached around the pyridine ring. This colorless liquid is a precursor to pyridine derivatives that have applications in the pharmaceutical and agricultural industries. Like pyridine, 3-methylpyridine is a colorless liquid with a strong odor and is classified as a weak base.

<span class="mw-page-title-main">Polyprenol</span> Chemical compound

Polyprenols are natural long-chain isoprenoid alcohols of the general formula H-(C5H8)n-OH, where n is the number of isoprene units. Any prenol with more than 4 isoprene units is a polyprenol. Polyprenols play an important function, acting as natural bioregulators and are found in small quantities in various plant tissues. Dolichols, which are found in all living creatures, including humans, are their 2,3-dihydro derivatives.

<span class="mw-page-title-main">Isoprenol</span> Chemical compound

Isoprenol, also known as 3-methylbut-3-en-1-ol, is a hemiterpene alcohol. It is produced industrially as an intermediate to 3-methylbut-2-en-1-ol (prenol): global production in 2001 can be estimated as 6–13 thousand tons.

1-Vinylimidazole is a water-soluble basic monomer that forms quaternizable homopolymers by free-radical polymerization with a variety of vinyl and acrylic monomers. The products are functional copolymers, which are used as oil field chemicals and as cosmetic auxiliaries. 1-Vinylimidazole acts as a reactive diluent in UV lacquers, inks, and adhesives.

Isophytol is a terpenoid alcohol that is used as a fragrance and as an intermediate in the production of vitamin E and K1.

Green solvents are environmentally friendly chemical solvents that are used as a part of green chemistry. They came to prominence in 2015, when the UN defined a new sustainability-focused development plan based on 17 sustainable development goals, recognizing the need for green chemistry and green solvents for a more sustainable future. Green solvents are developed as more environmentally friendly solvents, derived from the processing of agricultural crops or otherwise sustainable methods as alternatives to petrochemical solvents. Some of the expected characteristics of green solvents include ease of recycling, ease of biodegradation, and low toxicity.

References

  1. 1 2 3 4 5 3-Methyl-2-buten-1-ol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, May 2005.
  2. HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Agency, retrieved 2009-08-31[ permanent dead link ].
  3. See, e.g., Kogan, S. B.; Kaliya, M.; Froumin, N. (2006), "Liquid phase isomerization of isoprenol into prenol in hydrogen environment", Appl. Catal. A: Gen., 297 (2): 231–36, doi:10.1016/j.apcata.2005.09.010 .
  4. Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN   0471238961.
  5. See, e.g., Goodfellow, Robert D.; Huang, Yung-Sheng; Radtke, Harold E. Jr. (1972), "Isoprenol biosynthesis in the fly, Sarcophaga bullata", Insect Biochem., 2 (8): 467–75, doi:10.1016/0020-1790(72)90027-3 .
  6. Edlund, C.; Söderberg, M.; Kristensson, K. (1994), "Isoprenoids in aging and neurodegeneration", Neurochem. Int., 25 (1): 35–38, doi:10.1016/0197-0186(94)90050-7, PMID   7950967 .
  7. Company Announcement – Report on Opening of Tomsk Production Facility, Solagran Ltd., 2008-03-27, retrieved 2009-08-31.