Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid

Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid Property

Melting point:

144 °C(Solv: benzene (71-43-2))

Boiling point:

433.6±18.0 °C(Predicted)

Density 

1.329

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.80±0.10(Predicted)

color 

White to Almost white

InChI

InChI=1S/C12H15NO4/c14-10-5-6-11(15)13(10)7-8-1-3-9(4-2-8)12(16)17/h5-6,8-9H,1-4,7H2,(H,16,17)/t8-,9-

InChIKey

LQILVUYCDHSGEU-KYZUINATSA-N

SMILES

[C@@H]1(C(O)=O)CC[C@@H](CN2C(=O)C=CC2=O)CC1

CAS DataBase Reference

69907-67-1

Safety

HS Code 

2928009090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid Chemical Properties,Usage,Production

Description

Trans-4-(Maleimidomethyl) cyclohexanecarboxylic Acid is a kind of carboxylate, being well known for its N-hydroxysuccinimide ester derivative (SMCC), which is a useful cross-linking reagent. SMCC is widely used for the generation of stable maleimide-activated carrier proteins, enzyme immunoconjugates and hapten carrier molecule conjugates. It can be used for the coupling of a peptide to an amino group.

Synthesis

Step B: Maleamic acid (36.8 g, 144 mmol) and sodium acetate (13.6 g, 165 mmol) prepared in Step A were dissolved in acetic anhydride (368 mL), and the mixture was transferred to a sealed glass reaction vessel and heated to react for 3 hours at 120 °C. Upon completion of the reaction, the cooled black slurry reaction mixture was slowly poured into water (3 L), stirred thoroughly and extracted with dichloromethane. The organic layers were combined, dried with anhydrous sodium sulfate, filtered through a sintered glass funnel, and the filtrate was evaporated to dryness and dried under high vacuum to afford the target product trans-4-(maleimidomethyl)cyclohexanecarboxylic acid as a yellow solid (7.00 g, 20% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 6.73 (s, 2H), 3.40 (d, 2H, J = 7 Hz), 2.28 (m, 1H), 2.06 (m, 2H), 1.75 (m, 3H), 1.42 (m, 2H), 1.03 (m, 2H).

References

https://www.aatbio.com/products/smcc-4-n-maleimidomethyl-cyclohexanecarboxylic-acid-n-hydroxysuccinimide-ester-cas-64987-85-5
http://www.sigmaaldrich.com/catalog/product/sigma/m5525?lang=en&region=US
Zhang, Hongyan, et al. "Antifreeze protein detection using Rhodamine B as photoluminescence label inporous silicon." Current Applied Physics13.4(2013):736-742.