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M3933

Sigma-Aldrich

2-Methylisoborneol solution

~10 mg/mL in methanol, ≥98% (GC)

Synonym(s):

(1R-exo)-1,2,7,7-Tetramethylbicyclo[2.2.1]heptan-2-ol

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About This Item

Empirical Formula (Hill Notation):
C11H20O
CAS Number:
2371-42-8
Molecular Weight:
168.28
EC Number:
200-659-6
MDL number:
MFCD00082463
UNSPSC Code:
12352001
PubChem Substance ID:
57654381
NACRES:
NA.22

Quality Level

200

Assay

≥98% (GC)

concentration

~10 mg/mL in methanol

storage temp.

−20°C

SMILES string

CC1(C)[C@@H]2CC[C@@]1(C)[C@](C)(O)C2

InChI

1S/C11H20O/c1-9(2)8-5-6-10(9,3)11(4,12)7-8/h8,12H,5-7H2,1-4H3/t8-,10-,11-/m1/s1

InChI key

LFYXNXGVLGKVCJ-FBIMIBRVSA-N

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General description

2-Methylisoborneol (2-MIB) is a semi-volatile compound, responsible for the undesirable earthy-musty odor in surface water. It can be efficiently degraded by TiO2 photocatalysis. 2-MIB can also be easily adsorbed on granular activated carbon.

Application

2-Methylisoborneol can be used as a reactant:
  • To prepare N-[(1R,2R,4R)-1,4,7,7-tetramethylbicyclo[2.2.1]hept-2-yl]acetamide by reacting with acetonitrile in the presence of boron trifluoride etherate.
  • In the enantioselective total synthesis of geissoschizine as well as geissoschizol.

Other Notes

Fungal metabolite which contributes to the earthy odor in public water supplies.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

Target Organs

Eyes,Central nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

51.8 °F

Flash Point(C)

11 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Ultrasonically induced degradation of 2-methylisoborneol and geosmin.
Song W and O'Shea KE.
Water Research, 41(12), 2672-2678 (2007)
Activated carbon adsorption of the odorous compounds 2-methylisoborneol and geosmin.
J. Amer. Water Works Assoc., 223-228 (1977)
The destruction of 2-methylisoborneol and geosmin using titanium dioxide photocatalysis.
Lawton LA, et al.
Applied Catalysis. B, Environmental, 44(1), 9-13 (2003)
Mikael A Petersen et al.
Journal of agricultural and food chemistry, 59(23), 12561-12568 (2011-11-02)
Globally, aquaculture systems with water recirculation experience increasing problems with microbial taste and odor compounds (TOCs) such as geosmin and 2-methylisoborneol (MIB). This study investigated the content of geosmin and MIB in water and the flesh of 200 rainbow trouts
Marc Auffret et al.
FEMS microbiology ecology, 84(2), 235-247 (2012-12-12)
A variety of factors affecting water quality in recirculating aquaculture systems (RAS) are associated with the occurrence of off-flavours. In this study, we report the impact of water quality on the bacterial diversity and the occurrence of the geosmin-synthesis gene
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