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The monopalmityloxy shikimic acids have been synthesized from shikimic acid and palmitic acid catalyzed by Novozym 435 in 2-methyl-2-butanol. The anticoagulation activity in vivo via oral administration of monopalmityloxy shikimic acid has been evaluated through arteriovenous shunt model of rats and through the determination of thrombin time, prothrombin time, and activated partial thromboplastin time via rats. After reaction, the solid shikimic acid has been observed to dissolve in the reaction system completely. The subsequent high-performance liquid chromatography-mass spectroscopy analysis showed that the monopalmityloxy shikimic acids, as the only products, had been formed and the overall conversion rate was over 70%. The result showed that it had anti-thrombosis activity, could prolong the coagulating time and bleeding time in vivo, and lengthen the coagulating time in vitro. Compared with control group, the differences of the treatment group and aspirin group of rats are significant (P < 0.05) for prothrombin time and thrombin time, and very significant (P < 0.01) for activated partial thromboplastin time. It suggested that the product had the anticoagulation activity. The mechanism might be the co-action of the inhibition of intrinsic coagulation and the inhibition of extrinsic coagulation, and the inhibiting effect on intrinsic pathway is stronger than that on extrinsic pathway.