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Hipposudoric acid

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Hipposudoric acid
Names
Preferred 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
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H8O8/c17-6-1-2-7(18)11-10(6)13-12(14(11)16(23)24)8(19)3-5(15(13)22)4-9(20)21/h1-3,17H,4H2,(H,20,21)(H,23,24)Key: JTNHFMSBPHUJFI-UHFFFAOYSA-N
SMILES
  • O=C1C=CC(O)=C2C(C(C(CC(O)=O)=CC3=O)=O)=C3C(C(O)=O)=C12
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.

It has been both widely and falsely reported that hipposudoric acid colors hippo milk pink. This is not the case; hippo milk is white or beige in color.

Norhipposudoric acid

References

  1. Kimiko Hashimoto; Yoko Saikawa; Masaya Nakata (2007). "Studies on the red sweat of the Hippopotamus amphibius" (PDF). Pure Appl. Chem. 79 (4): 507–517. doi:10.1351/pac200779040507. S2CID 12944558.
  2. Yoko Saikawa; Kimiko Hashimoto; Teruyuki Komiya (2004). "The red sweat of the hippopotamus". Nature. 429 (6990): 363. Bibcode:2004Natur.429..363S. doi:10.1038/429363a. PMID 15164051. S2CID 4404922.
  3. 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. Archived from the original on 2012-02-17. Retrieved 2009-04-11.
  4. "FACT CHECK: Is Hippopotamus Milk Pink?". Snopes.com. 6 January 2016. Retrieved 2022-02-16.
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