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250856

Sigma-Aldrich

(1S,2S,3S,5R)-(+)-Isopinocampheol

98%

Synonym(s):

(1S,2S,3S,5R)-2,6,6-Trimethylbicyclo[3.1.1]heptan-3-ol, (1S,2S,3S,5R)-3-Pinanol, 3-Pinanol

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About This Item

Empirical Formula (Hill Notation):
C10H18O
CAS Number:
27779-29-9
Molecular Weight:
154.25
Beilstein:
2038104
EC Number:
248-657-4
MDL number:
MFCD00074780
UNSPSC Code:
12352001
PubChem Substance ID:
24855077

Assay

98%

form

solid

optical activity

[α]20/D +35.1°, c = 20 in ethanol

bp

219 °C (lit.)

mp

51-53 °C (lit.)

SMILES string

C[C@@H]1[C@@H](O)CC2CC1C2(C)C

InChI

1S/C10H18O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-9,11H,4-5H2,1-3H3/t6-,7+,8-,9-/m0/s1

InChI key

REPVLJRCJUVQFA-KZVJFYERSA-N

General description

(1S,2S,3S,5R)-(+)-Isopinocampheol is a chiral terpenol.

Application

(1S,2S,3S,5R)-(+)-Isopinocampheol may be used in the preparation of
  • thermotropic chiral nematic side-chain copolymers
  • ortho-(diphenylphosphino)phenylphosphonous acid di[(1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]-hept-3-yl]ester, a phosphino-phosphonite ligand
  • O,O´bis[(1S,2S,3S,5R)2,6,6-trimethylbicyclo[3.1.1]hept-3-yl] dithiophosphoric acid, a bioactive compound with antifungal effect

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

200.1 °F - closed cup

Flash Point(C)

93.4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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New thermotropic chiral nematic copolymers using (1S, 2S, 3S, 5R)-(+)-and (1R, 2R, 3R, 5S)-([minus])-isopinocampheol as building blocks.
Chen SH and Tsai ML.
Macromolecules, 23(24) (1990)
Synthesis of enantiopure C 1 symmetric diphosphines and phosphino-phosphonites with ortho-phenylene backbones.
Kottsieper KW, et al.
Tetrahedron Asymmetry, 12(8), 1159-1169 (2001)
Chiral phosphorus dithio acids derived from (1S, 2S, 3S, 5R)-(+)-isopinocampheol. Synthesis and fungicidal activity.
Nizamov IS, et al.
Russian Chemical Bulletin, 61(12), 2370-2371 (2012)
Terpene Analogues of Dithiophospate Pesticides.
Cherkasov RA, et al.
Phosph. Sulfur Relat. Elem., 186(4), 1003-1004 (2011)

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