This paper focuses on exploring formation and development of Japanese adverbs ‘TAKADAKA’ and ‘TAKAGA’ that can be mainly seen in the Late Middle and Early Modern Japanese. ‘TAKADAKA’ and ‘TAKAGA’ are synonymous on the basis of ‘TAKA(高, high)’ in terms of word structure. As a result, historically, compared to Takaga, adverbization of ‘TAKADAKA’ (initially (before the Middle Ages) was preceded by ‘ni’　and ‘to’, but like modern words ‘TAKAGA’ was used earlier in the example of negative evaluation such as “it is not a big deal (even if we estimate a lot)”. In the scope of this survey, ‘TAKAGA’　can be confirmed from the early modern materials (after the late 17C), and ‘TAKADAKA’ can be confirmed from the late modern materials (after 19C). Both were expressed by the noun ‘TAKA(高, high)’ from the Middle Ages, meaning estimate the total amount and its level. From the point of view of desirability, both have a negative evaluation. Based on present results, it is necessary to examine the case of adverbization that expresses the speaker’s value judgment and evaluation from a chronological perspective.