p-Menthane-3,8-diol

Product Namep-Menthane-3,8-diol
CAS42822-86-6
MFC10H20O2
MW172.27
EINECS255-953-7
MOL File42822-86-6.mol

Chemical Properties

Melting point	82-83 °C
Boiling point	267.6±8.0 °C(Predicted)
Density	1.009±0.06 g/cm3(Predicted)
FEMA	4053 \| P-MENTHANE-3,8-DIOL
storage temp.	Sealed in dry,Room Temperature
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Solid
pka	15.18±0.29(Predicted)
color	Off-White
Odor	at 10.00 % in dipropylene glycol. minty herbal eucalyptus
Odor Type	herbal
JECFA Number	1416
Cosmetics Ingredients Functions	SKIN CONDITIONING HAIR CONDITIONING ORAL CARE
InChI	InChI=1S/C10H20O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-9,11-12H,4-6H2,1-3H3
InChIKey	LMXFTMYMHGYJEI-UHFFFAOYSA-N
SMILES	C(C1CCC(C)CC1O)(O)(C)C
LogP	1.37
EPA Substance Registry System	p-Menthane-3,8-diol (42822-86-6)

Usage And Synthesis

Definition

P-menthane-3,8-diol is a p-menthane monoterpenoid in which p-menthane carries hydroxy groups at C-3 and C-8. P-menthane-3,8-diol derives from a hydride of a p-menthane.

Uses

p-Menthane-3, 8-diol, also known as para-menthane-3, 8-diol and PMD, is an active ingredient used in insect repellents. p-Menthane-3, 8-diol smells similar to menthol and acts as a coolant.
P-menthane-3,8-diol is used to make products that are applied to human skin and clothing for the purpose of repelling insects, such as mosquitoes, biting flies and gnats. P-menthane-3,8-diol can be used in two types of consumer pesticide products: a spray and a lotion.

Description

p-Menthane-3,8-diol, also known as para-menthane-3,8-diol, PMD, or menthoglycol, is an active ingredient used in insect repellents. It smells similar to menthol and has a cooling feel. There are eight possible isomers of p-Menthane-3,8-diol, and the exact composition is rarely specified and is commonly assumed to be a complex mixture.
Refined OLE contains approximately 64% p-Menthane-3,8-diol (a mixture of the cis and trans isomers of p-menthane-3,8-diol). 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 "p-Menthane-3,8-diol 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 "p-Menthane-3,8-diol and related oil of lemon eucalyptus compounds".

Chemical Properties

p-Menthane-3,8-diol has a faint minty, herbaceous, eucalyptus-like odor. The cooling power is reported to be approxi mately 9.5 times that of (-)-menthol.

Occurrence

Reportedly present in the lemon eucalyptus plant(Eucalyptus citriodora tree), which is native to Australia, but is now cultivated in many warm places around the world.

Uses

2-Hydroxy-α,α,4-trimethylcyclohexanemethanol is used in protection measures in the prevention of tick-born diseases. Acaricide.

Preparation

In a patented method, citronellal is treated with aqueous sulfuric acid to produce p-menthane-3,8-diol. Also produced by an extraction process utilizing lemon eucalyptus oil.

Definition

ChEBI: P-menthane-3,8-diol is a p-menthane monoterpenoid in which p-menthane carries hydroxy groups at C-3 and C-8. It derives from a hydride of a p-menthane.