Hipposudoric acid

Hipposudoric acid

Names
IUPAC name 3-Carboxymethyl-5-hydroxy-1,4,8-trioxo-4,8-dihydro-1H-fluorene-9-carboxylic acid
Identifiers
CAS Number	851367-73-2
ChemSpider	21474973
Jmol interactive 3D	Image
InChI InChI=1S/C15H6O8/c16-5-1-2-6(17)9-8(5)11-10(12(9)15(22)23)7(18)3-4(13(11)19)14(20)21/h1-3,16H,(H,20,21)(H,22,23) Key: VQUMVNJFHSBVDL-UHFFFAOYSA-N InChI=1/C15H6O8/c16-5-1-2-6(17)9-8(5)11-10(12(9)15(22)23)7(18)3-4(13(11)19)14(20)21/h1-3,16H,(H,20,21)(H,22,23) Key: VQUMVNJFHSBVDL-UHFFFAOYAR
SMILES c1cc(=O)c-2c(c3=c(c2c1O)c(=O)c(cc3=O)C(=O)O)C(=O)O
Properties
Chemical formula	C16H8O8
Molar mass	328.23 g·mol^−1
Appearance	Red
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Hipposudoric acid is a red pigment found in the skin secretions of the hippopotamus;^[1] although the secretions are often known as "blood sweat" (thus the name "hipposudoric", referring to "hippo sweat"), they are neither blood nor sweat.

Like its orange-colored analog norhipposudoric acid, hipposudoric acid functions both as a natural sunscreen and as an antimicrobial agent. It is derived from the oxidative dimerization of homogentisic acid.^[2]

Norhipposudoric acid

References

1. Kimiko Hashimoto, Yoko Saikawa, and Masaya Nakata (2007). "Studies on the red sweat of the Hippopotamus amphibius" (PDF). Pure Appl. Chem. 79 (4): 507–517. doi:10.1351/pac200779040507.
2. Moriya Kai, Matsuura Masanori, Saikawa Yoko, Hashimoto Kimiko, Yamaguguchi Ayumu, Sakamoto Kazuhiro, Akihisa Narito, Hirata Hiroyoshi (2006). "Properties of the enzyme responsible to the synthesis of hipposudoric and norhipposudoric acids, the pigments in the red sweat of the hippopotamus". Nippon Kagakkai Koen Yokoshu 86 (2): 1314.