Chlorogenic acid
Chemical compound
From Wikipedia, the free encyclopedia
Chlorogenic acid (CGA) is the ester of caffeic acid and quinic acid, functioning as an intermediate in lignin biosynthesis.[1]
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| Names | |
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| Preferred IUPAC name
(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid | |
| Other names
3-(3,4-Dihydroxycinnamoyl)quinate 3-(3,4-Dihydroxycinnamoyl)quinic acid 3-Caffeoylquinate 3-Caffeoylquinic acid 3-CQA 3-O-Caffeoylquinic acid Chlorogenate Chlorogenic acid Heriguard 3-trans-Caffeoylquinic acid 5-O-Caffeoylquinic acid | |
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CompTox Dashboard (EPA) |
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| Properties | |
| C16H18O9 | |
| Molar mass | 354.311 g·mol−1 |
| Density | 1.28 g/cm3 |
| Melting point | 207 to 209 °C (405 to 408 °F; 480 to 482 K) |
| Hazards | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
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| Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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History and nomenclature
The ester of caffeic acid and quinic acid was identified in 1932.[2] Subsequently, the scope of this family of conjugates was shown to be great. Chlorogenic acids are now recognized as being widespread in plants, including many foods.
Despite the "chloro" of the name, chlorogenic acids contain no chlorine. Instead, the name comes from the Greek χλωρός (khloros, light green) and -γένος (genos, a suffix meaning "giving rise to"), pertaining to the green color produced when chlorogenic acids are oxidized.
Structural properties
Structurally, chlorogenic acid is the ester formed between caffeic acid and the 3-hydroxyl of L-quinic acid.[3][4] Isomers of chlorogenic acid include the caffeoyl ester at other hydroxyl sites on the quinic acid ring: 4-O-caffeoylquinic acid (cryptochlorogenic acid or 4-CQA) and 5-O-caffeoylquinic acid (neochlorogenic acid or 5-CQA). The epimer at position 1 has not yet been reported.[5]
Structures having more than one caffeic acid group are called isochlorogenic acids, and can be found in coffee.[6] There are several isomers, such as 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid.[7] and cynarine (1,5-dicaffeoylquinic acid)
Biosynthesis and natural occurrence
The biosynthetic precursor to chlorogenic acid is 4-coumaroyl-CoA, containing a single hydroxyl group on the aryl ring, which in turn is produced from cinnamic acid. The hydroxylation of the coumaryl ester, i.e. installing the second hydroxy group, is catalyzed by a cytochrome P450 enzyme.[8]
Chlorogenic acid can be found in the bamboo Phyllostachys edulis,[9] as well as in many other plants,[10] such as the shoots of common heather (Calluna vulgaris).[11]
In food
Chlorogenic acid and the related compounds cryptochlorogenic acid, and neochlorogenic acid have been found in the leaves of Hibiscus sabdariffa.[12] Isomers of chlorogenic acid are found in potatoes.[13] Chlorogenic acid is present in the flesh of eggplants,[14] peaches,[15] prunes[16] and coffee beans.[17]
Research and safety
There is not enough evidence to determine whether chlorogenic acid is safe or effective for human health, and its use in high doses, such as excessive consumption of green coffee, may have adverse effects.[18] Chlorogenic acid has not been approved as a prescription drug or food additive recognized as a safe ingredient for foods or beverages.[19]
Chlorogenic acid is under preliminary research for its possible biological effects, such as regulation of blood pressure, although there is insufficient evidence for its effectiveness.[18][20][21][22]