Naphthoquinone
Naphthoquinone (pronunciation: /næf.θoʊ.kwiː.noʊn/) is a class of organic compounds that are structurally related to naphthalene. The most notable members of this class are Vitamin K, juglone, and plumbagin.
Etymology
The term "Naphthoquinone" is derived from naphthalene, a type of polycyclic aromatic hydrocarbon, and quinone, a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds", resulting in "a fully conjugated cyclic dione structure".
Chemistry
Naphthoquinones are made by oxidation of naphthalene or its derivatives. They are yellow to greenish-yellow crystalline solids that are often used in industry as dyes. The structure of naphthoquinones is based on two benzene rings fused together, with two carbonyl groups attached at the 1 and 4 positions of the fused ring system.
Biological Importance
Naphthoquinones are found in many natural sources and are often associated with significant biological activity. For example, Vitamin K, a naphthoquinone, is essential for the functioning of several proteins involved in blood clotting, bone metabolism, and heart health. Other naphthoquinones, such as juglone and plumbagin, have been studied for their potential anticancer properties.
Related Terms
- Naphthalene: A polycyclic aromatic hydrocarbon from which naphthoquinones are derived.
- Quinone: A class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds", resulting in "a fully conjugated cyclic dione structure".
- Vitamin K: A naphthoquinone that is essential for the functioning of several proteins involved in blood clotting, bone metabolism, and heart health.
- Juglone: A naphthoquinone found in the black walnut tree that has been studied for its potential anticancer properties.
- Plumbagin: A naphthoquinone found in the plumbago plant that has been studied for its potential anticancer properties.
External links
- Medical encyclopedia article on Naphthoquinone
- Wikipedia's article - Naphthoquinone
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