P-Menthane-3,8-diol

Last updated
p-Menthane-3,8-diol
P-menthane-3,8-diol (PMD).svg
P-menthane-3,8-diol 3D BS.png
Names
Preferred IUPAC name
2-(2-Hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
Other names
2-(1-Hydroxy-1-methylethyl)-5-methylcyclohexanol
para-Menthane-3,8-diol
2-Hydroxy-α,α,4-trimethylcyclohexanemethanol
Identifiers
3D model (JSmol)
2552262
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.050.849 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 255–9537
KEGG
PubChem CID
UNII
  • InChI=1S/C10H20O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-9,11-12H,4-6H2,1-3H3 Yes check.svgY
    Key: LMXFTMYMHGYJEI-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H20O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-9,11-12H,4-6H2,1-3H3
    Key: LMXFTMYMHGYJEI-UHFFFAOYAL
  • OC(C1CCC(CC1O)C)(C)C
Properties
C10H20O2
Molar mass 172.268 g·mol−1
Density 1.009 g/cm3
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 ?)

p-Menthane-3,8-diol, also known as para-menthane-3,8-diol, PMD, or menthoglycol, is an organic compound classified as a diol and a terpenoid. It is colorless. Its name reflects the hydrocarbon backbone, which is that of p-menthane. A total of eight stereoisomers are possible, based on the three stereocenters of the ring. Depending on the source, one or more may predominate.

Contents

PMD is the active ingredient in some insect repellents. Its odor and chemical structure are similar to menthol, and it has a cooling feel. [1] It is found in small quantities in the essential oil from the leaves of Corymbia citriodora , formerly known as Eucalyptus citriodora. This tree is native to Australia, but is now cultivated in many warm places around the world. C. citriodora oil, when refined to increase its PMD content for use in insect repellents, is known in the United States as oil of lemon eucalyptus (OLE). [2] C. citriodora oil contains only 1–2% PMD, while refined OLE contains approximately up to 70% PMD. [3] Some commercial PMD products are not made from C. citriodora oil, but rather from synthetic citronellal.

Effectiveness

A 2006 study showed that PMD used as a repellent is as effective as DEET when used in like quantities. [4]

Contraindications

PMD should not be used on children under 3 years of age. [5]

Interactions

Few if any studies have evaluated possible interactions when using PMD with sunscreens. [6]

Chemistry

There are eight possible stereoisomers. [7] The exact composition is rarely specified and is commonly assumed to be a complex mixture. PMD can be synthesized by a Prins reaction of citronellal. [3]

Refined OLE contains approximately up to 70% PMD, a mixture of the cis and trans isomers of p-menthane-3,8-diol.

History

Its repellent effect was discovered in the 1960s by the industry.[ vague ]

OLE has been notified under the European Biocidal Products Directive (BPD) 98/8/EC (now BPR Regulation (EU) No. 528/212) under its generic name "PMD rich botanic oil" and is currently proceeding through the registration process with the Health and Safety Executive in the UK. It is also registered with Canada's Pest Management Regulatory Agency under the generic name "PMD and related oil of lemon eucalyptus compounds".

See also

Related Research Articles

<span class="mw-page-title-main">Menthol</span> Organic compound used as flavouring and analgesic

Menthol is an organic compound, more specifically a monoterpenoid, made synthetically or obtained from the oils of corn mint, peppermint, or other mints. It is a waxy, clear or white crystalline substance, which is solid at room temperature and melts slightly above.

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

N,N-Diethyl-meta-toluamide, also called diethyltoluamide or DEET, is the oldest, most effective and most common active ingredient in commercial insect repellents. It is a slightly yellow oil intended to be applied to the skin or to clothing and provides protection against mosquitoes, flies, ticks, fleas, chiggers, leeches, and many other biting insects.

PMD may refer to:

<span class="mw-page-title-main">Citronella oil</span> Fragrant essential oil derived from lemongrass

Citronella oil is an essential oil obtained from the leaves and stems of different species of Cymbopogon (lemongrass). The oil is used extensively as a source of perfumery chemicals such as citronellal, citronellol, and geraniol. These chemicals find extensive use in soap, candles and incense, perfumery, cosmetic, and flavouring industries throughout the world.

<span class="mw-page-title-main">Sandfly</span> Name of several types of blood-sucking fly

Sandfly or sand fly is a colloquial name for any species or genus of flying, biting, blood-sucking dipteran (fly) encountered in sandy areas. In the United States, sandfly may refer to certain horse flies that are also known as "greenheads", or to members of the family Ceratopogonidae. The bites usually result in a small, intensely itchy bump or welt, the strength of which intensifies over a period of 5-7 days before dissipating. Moderate relief is achieved with varying success through the application of over the counter products such as Benadryl (ingested) or an analgesic cream such as After Bite. Outside the United States, sandfly may refer to members of the subfamily Phlebotominae within the Psychodidae. Biting midges (Ceratopogonidae) are sometimes called sandflies or no-see-ums. New Zealand sandflies are in the genus of sand fly Austrosimulium, a type of black fly.

<span class="mw-page-title-main">Insect repellent</span> Substance which repels insects

An insect repellent is a substance applied to the 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).

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

Citronellal or rhodinal (C10H18O) is a monoterpenoid aldehyde, the main component in the mixture of terpenoid chemical compounds that give citronella oil its distinctive lemon scent.

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

Citral is an acyclic monoterpene aldehyde. Being a monoterpene, it is made of two isoprene units. Citral is a collective term which covers two geometric isomers that have their own separate names; the E-isomer is named geranial or citral A. The Z-isomer is named neral or citral B. These stereoisomers occur as a mixture, not necessarily racemic; e.g. in essential oil of Australian ginger, the neral to geranial ratio is 0.61.

<i>Backhousia citriodora</i> Species of tree

Backhousia citriodora is a flowering plant in the family Myrtaceae, genus Backhousia. It is endemic to subtropical rainforests of central and south-eastern Queensland, Australia, with a natural distribution from Mackay to Brisbane.

Icaridin, also known as picaridin, is an insect repellent which can be used directly on skin or clothing. It has broad efficacy against various arthropods such as mosquitos, ticks, gnats, flies and fleas, and is almost colorless and odorless. A study performed in 2010 showed that picaridin spray and cream at the 20% concentration provided 12 hours of protection against ticks. Unlike DEET, icaridin does not dissolve plastics, synthetics or sealants, is odorless and non-greasy and presents a lower risk of toxicity when used with sunscreen, as it may reduce skin absorption of both compounds.

<span class="mw-page-title-main">Eucalyptus oil</span> Distilled oil from the leaf of Eucalyptus

Eucalyptus oil is the generic name for distilled oil from the leaf of Eucalyptus, a genus of the plant family Myrtaceae native to Australia and cultivated worldwide. Eucalyptus oil has a history of wide application, as a pharmaceutical, antiseptic, repellent, flavouring, fragrance and industrial uses. The leaves of selected Eucalyptus species are steam distilled to extract eucalyptus oil.

<span class="mw-page-title-main">Off! (brand)</span> Brand of insect repellant

Off! (stylized as OFF!) is an insect repellent brand from S. C. Johnson & Son, produced in Finland. Its active ingredient is DEET (N,N-diethyl-m-toluamide) or metofluthrin which is the most common ingredient in insect repellants. It was first sold in 1957.

<i>Corymbia citriodora</i> Species of plant

Corymbia citriodora, commonly known as lemon-scented gum and other common names, is a species of tall tree that is endemic to north-eastern Australia. It has smooth white to pink bark, narrow lance-shaped to curved adult leaves, flower buds in groups of three, white flowers and urn-shaped or barrel-shaped fruit.

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

Cubebol is a natural sesquiterpene alcohol first identified in cubeb oil. It is also found in basil. It was patented as a cooling agent in 2001 by Firmenich, an international flavor company. The taste of cubebol is cooling and refreshing. The patent describes application of cubebol as a refreshing agent in various products, ranging from chewing gum to sorbets, drinks, toothpaste, and gelatin-based confectioneries.

<span class="mw-page-title-main">Catnip</span> 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>Aedes triseriatus</i> Species of mosquito

Aedes triseriatus is a member of the true fly order. It is called the eastern tree hole mosquito due to its predilection towards breeding in stagnant water that is found in natural holding containers such as tree holes. It is native to the eastern United States and southern Canada and favors hardwood habitats. It has been found as far south as the Florida Keys, as far west as Idaho and Utah, and as far north as Quebec and Ontario. This species has not yet been found in Europe, but it has the potential to spread through international trade. In 2004, it was found in a shipment of tires travelling from Louisiana to France, but it was identified and targeted with insecticides that truncated its spread. It is a known vector of La Crosse encephalitis and canine heartworm disease. In the laboratory, it has been found to vector several other viruses including yellow fever, eastern encephalitis, Venezuelan encephalitis, and western encephalitis. Because of its potential for international spread and its proclivity for transmitting disease, monitoring the distribution of this species is essential.

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

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References

  1. John C. Leffingwell. "Cool without menthol & cooler than menthol and cooling compounds as insect repellents". Leffingwell & Associates.
  2. "Home". citrepel.co.uk.
  3. 1 2 Drapeau, Jeremy (2011). "Green synthesis of para-Menthane-3,8-diol from Eucaplytus citriodora: Application for repellent products". Comptes Rendus Chimie. 14 (7–8): 629–635. doi:10.1016/j.crci.2011.02.008. Open Access logo PLoS transparent.svg
  4. Carroll, Scott P.; Loye, Jenella (2006). "PMD, a Registered Botanical Mosquito Repellent with Deet-Like Efficacy". Journal of the American Mosquito Control Association. 22 (3): 507–13. doi:10.2987/8756-971X(2006)22[507:PARBMR]2.0.CO;2. PMID   17067054. S2CID   225645.
  5. "Prevent Mosquito Bites". Centers for Disease Control and Prevention. Retrieved 24 September 2023.
  6. "Insect Repellents". National Pesticide Information Center. February 2018. Archived from the original on 13 September 2023. Retrieved 26 September 2023. Few or no studies address using IR3535 or oil of lemon eucalyptus with sunscreens.
  7. PubChem Compound Search