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400416

Sigma-Aldrich

(1R,2R,5R)-(+)-2-Hydroxy-3-pinanone

99%

Synonym(s):

(1R,2R,5R)-2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

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About This Item

Empirical Formula (Hill Notation):
C10H16O2
CAS Number:
24047-72-1
Molecular Weight:
168.23
Beilstein:
2249018
MDL number:
MFCD19237371
UNSPSC Code:
12352000
PubChem Substance ID:
24864915
NACRES:
NA.22
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Assay

99%

form

solid

optical activity

[α]20/D +39°, c = 0.5 in chloroform

bp

245 °C (lit.)

mp

37-39 °C (lit.)

density

1.059 g/mL at 25 °C (lit.)

functional group

hydroxyl
ketone

SMILES string

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

InChI

1S/C10H16O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-7,12H,4-5H2,1-3H3/t6-,7-,10?/m1/s1

InChI key

VZRRCQOUNSHSGB-KTWZPZHPSA-N

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This Item
287784327956268070
(1R,2R,5R)-(+)-2-Hydroxy-3-pinanone 99%

400416

(1R,2R,5R)-(+)-2-Hydroxy-3-pinanone

(1R,2R,3S,5R)-(−)-Pinanediol 99%

287784

(1R,2R,3S,5R)-(−)-Pinanediol

(1R)-(+)-Nopinone 98%

327956

(1R)-(+)-Nopinone

(+)-α-Pinene ≥99%

268070

(+)-α-Pinene

assay

99%

assay

99%

assay

98%

assay

≥99%

mp

37-39 °C (lit.)

mp

57-59 °C (lit.)

mp

-

mp

−62 °C (lit.)

density

1.059 g/mL at 25 °C (lit.)

density

-

density

0.981 g/mL at 25 °C (lit.)

density

0.858 g/mL at 20 °C (lit.)

bp

245 °C (lit.)

bp

101-102 °C/1 mmHg (lit.)

bp

209 °C (lit.)

bp

155-156 °C (lit.)

form

solid

form

-

form

liquid

form

liquid

optical activity

[α]20/D +39°, c = 0.5 in chloroform

optical activity

[α]21/D −8.6°, c = 6.5 in toluene

optical activity

[α]20/D +16°, neat

optical activity

[α]21/D +50.7°, neat

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

222.8 °F - closed cup

Flash Point(C)

106 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves
  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    BGBC4628V
    BGBC2589V
    BGBC0364V
    BGBB7419
    1419160V

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    H Yamamoto et al.
    Applied microbiology and biotechnology, 67(1), 33-39 (2004-09-01)
    Formate dehydrogenases (FDH) are useful for the regeneration of NADH, which is required for asymmetric reduction by several dehydrogenases and reductases. FDHs have relatively low activity and are labile, especially to alpha-haloketones, thus FDH cannot be applied to the industrial
    Zhinan Xu et al.
    Applied microbiology and biotechnology, 70(1), 40-46 (2005-09-22)
    Escherichia coli M15 (pQE30-car0210) was constructed to express carbonyl reductase (CAR) by cloning the car gene from Candida magnoliae and inserting it into pQE30. By cultivating E. coli M15 (pQE30-car0210) and M15 (pQE30-gdh0310), 8.2-fold and 12.3-fold enhancements in specific enzymatic
    Hou Cao et al.
    Bioresource technology, 102(2), 1733-1739 (2010-10-12)
    A novel NADH-dependent dehydrogenases/reductases (SDRs) superfamily reductase (PsCRII) was isolated from Pichia stipitis. It produced ethyl (S)-4-chloro-3-hydroxybutanoate [(S)-CHBE] in greater than 99% enantiomeric excess. This enzyme was purified to homogeneity by ammonium sulfate precipitation followed by Q-Sepharose chromatography. Compared to
    Y Saratani et al.
    Bioscience, biotechnology, and biochemistry, 65(7), 1676-1679 (2001-08-23)
    The enantioselectivity of ECAA to ECHB by eight fungi of four genus was evaluated. All strains showed (S)-selectivity, and Cylindrocarpon sclerotigenum IFO 31855 gave the highest yield and good optical purity (e.e.; >99%). Cell-free extract and acetone-dried cells of C.
    M Kataoka et al.
    Applied microbiology and biotechnology, 51(4), 486-490 (1999-05-26)
    The asymmetric reduction of ethyl 4-chloro-3-oxobutanoate (COBE) to ethyl (R)-4-chloro-3-hydroxybutanoate [(R)-CHBE] using Escherichia coli cells, which coexpress both the aldehyde reductase gene from Sporobolomyces salmonicolor and the glucose dehydrogenase (GDH) gene from Bacillus megaterium as a catalyst was investigated. In
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