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404411

Sigma-Aldrich

(R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

98%

Synonym(s):

(R,R)-Jacobsen’s ligand

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About This Item

Linear Formula:
[[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10
CAS Number:
135616-40-9
Molecular Weight:
546.83
Beilstein:
5464823
MDL number:
MFCD00191800
UNSPSC Code:
12352116
PubChem Substance ID:
24865244
NACRES:
NA.22
Pricing and availability is not currently available.

Assay

98%

form

solid

optical activity

[α]20/D −315±15°, c = 1 in methylene chloride

mp

205-207 °C (lit.)

functional group

imine

SMILES string

CC(C)(C)c1cc(\C=N\[C@@H]2CCCC[C@H]2\N=C\c3cc(cc(c3O)C(C)(C)C)C(C)(C)C)c(O)c(c1)C(C)(C)C

InChI

1S/C36H54N2O2/c1-33(2,3)25-17-23(31(39)27(19-25)35(7,8)9)21-37-29-15-13-14-16-30(29)38-22-24-18-26(34(4,5)6)20-28(32(24)40)36(10,11)12/h17-22,29-30,39-40H,13-16H2,1-12H3/b37-21+,38-22+/t29-,30-/m1/s1

InChI key

FYNXDGNCEBQLGC-LQWPWIHBSA-N

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Application

Amylases from Aspergillus oryzae are used to prevent staling in the baking industry, clarify haze from fruit juices and alcoholic beverages, and produce glucose and maltose syrup products.
Versatile ligand for asymmetric catalysis.[1] Ligand used for preparing Jacobsen′s catalyst suitable for enantioselective epoxidation of olefins lacking functional groups.[2][3][4]

Lipases are used industrially for the resolution of chiral compounds and the transesterification production of biodiesel.

Biochem/physiol Actions

α-amylase catalyzes the hydrolysis of internal α-1,4-O-glycosidic bonds in starches to release α-anomeric sugars.
Lipases catalyze the hydrolysis of triacylglycerols into glycerol and free fatty acids.

Legal Information

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS7067
MKCR8237
MKCN6382
MKCM8667
MKCL3212

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Find documentation for the products that you have recently purchased in the Document Library.

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Journal of the American Chemical Society, 113, 7063-7063 (1991)
S. Chang et al.
The Journal of Organic Chemistry, 58, 6939-6939 (1993)
L. Deng et al.
The Journal of Organic Chemistry, 57, 4320-4320 (1992)
E.N. Jacobsen et al.
Journal of the American Chemical Society, 113, 7063-7063 (1991)

Articles

Salen Ligands

The first reports of salen used as ligands with manganese for asymmetric epoxidation reactions.

Salen Ligands

The first reports of salen used as ligands with manganese for asymmetric epoxidation reactions.

Salen Ligands

The first reports of salen used as ligands with manganese for asymmetric epoxidation reactions.

Salen Ligands

The first reports of salen used as ligands with manganese for asymmetric epoxidation reactions.

Chromatograms

application for HPLCapplication for HPLC

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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