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Hipposudoric acid

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Hipposudoric acid
Names
IUPAC name 3-Carboxymethyl-5-hydroxy-1,4,8-trioxo-4,8-dihydro-1H-fluorene-9-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
CompTox Dashboard (EPA)
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
  • 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 328.232 g·mol
Appearance Red
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Hipposudoric acid is a red pigment found in the skin secretions of the hippopotamus; 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.

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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