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900982

Sigma-Aldrich

Menthide

≥98.0%

Synonym(s):

(4R,7S)-4-methyl-7-(1-methylethyl)oxepan-2-one

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About This Item

Empirical Formula (Hill Notation):
C10H18O2
CAS Number:
Molecular Weight:
170.25
EC Number:
UNSPSC Code:
12162002

Assay

≥98.0%

form

liquid

color

colorless to pale yellow

storage temp.

−20°C

InChI

1S/C10H18O2/c1-7(2)9-5-4-8(3)6-10(11)12-9/h7-9H,4-6H2,1-3H3

InChI key

GGAXPLCKKANQED-UHFFFAOYSA-N

General description

Menthide is a seven-membered, plant-derived lactone monomer that can be readily polymerized via ring opening polymerization (ROP). Controlled ROP has yielded aliphatic polyesters with high molecular weights and narrow molecular weight distributions (PDI). Menthide has been copolymerized with other biologically derived monomers, such as lactide, to yield products such as thermoplastic elastomers and pressure-sensitive adhesives.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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James A Wilson et al.
Biomacromolecules, 16(10), 3191-3200 (2015-09-18)
We report the one-pot copolymerization of ω-pentadecalactone (PDL) to produce tri- and diblock-like copolymers with the ability to undergo postpolymerization modification. The ε-substituted ε-lactone (εSL), menthide (MI), was copolymerized with PDL to introduce side chain functionality into poly(ω-pentadecalactone) (PPDL) copolymers.
Polyurethanes based on renewable polyols from bioderived lactones.
Gurusamy-Thangavelu SA, et al.
Polym. Chem., 3, 2941-2948 (2012)
Jihoon Shin et al.
Biomacromolecules, 13(11), 3833-3840 (2012-10-16)
Renewable ABA triblock copolymers were prepared by sequential polymerization of the plant-based monomers menthide and α-methylene-γ-butyrolactone (MBL or tulipalin A). Ring-opening transesterification polymerization of menthide using diethylene glycol as an initiator gave α,ω-dihydroxy poly(menthide) (HO-PM-OH), which was converted to α,ω-dibromo

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