Hipposudoric acid

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Hipposudoric acid
Hipposudoric acid.png
Hipposudoric.png
Names
Preferred IUPAC name
3-(Carboxymethyl)-5-hydroxy-1,4,8-trioxo-4,8-dihydro-1H-fluorene-9-carboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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) Yes check.svgY
    Key: JTNHFMSBPHUJFI-UHFFFAOYSA-N Yes check.svgY
  • O=C1C=CC(O)=C2C(C(C(CC(O)=O)=CC3=O)=O)=C3C(C(O)=O)=C12
Properties
C16H8O8
Molar mass 328.232 g·mol−1
AppearanceRed
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [2] It is derived from the oxidative dimerization of homogentisic acid. [3]

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. [4]

Norhipposudoric acid Norhipposudoric acid.png
Norhipposudoric acid

Related Research Articles

<span class="mw-page-title-main">Hippopotamus</span> Large semi-aquatic mammal native to sub-Saharan Africa

The hippopotamus, also shortened to hippo, further qualified as the common hippopotamus, Nile hippopotamus, or river hippopotamus, is a large semiaquatic mammal native to sub-Saharan Africa. It is one of only two extant species in the family Hippopotamidae, the other being the pygmy hippopotamus. Its name comes from the ancient Greek for "river horse" (ἱπποπόταμος).

<span class="mw-page-title-main">Artiodactyl</span> Order of mammals

Artiodactyls are mammals belonging to the order Artiodactyla. Typically, they are ungulates which bear weight equally on two of their five toes: the third and fourth, often in the form of a hoof. The other three toes are either present, absent, vestigial, or pointing posteriorly. By contrast, most perissodactyls bear weight on an odd number of the five toes. Another difference between the two is that many artiodactyls digest plant cellulose in one or more stomach chambers rather than in their intestine as perissodactyls do. The advent of molecular biology, along with new fossil discoveries, found that cetaceans fall within this taxonomic branch, being most closely related to hippopotamuses. Some modern taxonomists thus apply the name Cetartiodactyla to this group, while others opt to include cetaceans within the existing name of Artiodactyla. Some researchers use "even-toed ungulates" to exclude cetaceans and only include terrestrial artiodactyls, making the term paraphyletic in nature.

<span class="mw-page-title-main">Hippopotamidae</span> Family of mammals

Hippopotamidae is a family of stout, naked-skinned, and semiaquatic artiodactyl mammals, possessing three-chambered stomachs and walking on four toes on each foot. While they resemble pigs physiologically, their closest living relatives are the cetaceans. They are sometimes referred to as hippopotamids.

<span class="mw-page-title-main">Pygmy hippopotamus</span> Small species of hippopotamus from West Africa

The pygmy hippopotamus or pygmy hippo is a small hippopotamid which is native to the forests and swamps of West Africa, primarily in Liberia, with small populations in Sierra Leone, Guinea, and Ivory Coast. It has been extirpated from Nigeria.

<span class="mw-page-title-main">Perspiration</span> Fluid secreted from sudoriferous glands

Perspiration, also known as sweat, is the fluid secreted by sweat glands in the skin of mammals.

<span class="mw-page-title-main">Digestion</span> Biological process of breaking down food

Digestion is the breakdown of large insoluble food compounds into small water-soluble components so that they can be absorbed into the blood plasma. In certain organisms, these smaller substances are absorbed through the small intestine into the blood stream. Digestion is a form of catabolism that is often divided into two processes based on how food is broken down: mechanical and chemical digestion. The term mechanical digestion refers to the physical breakdown of large pieces of food into smaller pieces which can subsequently be accessed by digestive enzymes. Mechanical digestion takes place in the mouth through mastication and in the small intestine through segmentation contractions. In chemical digestion, enzymes break down food into the small compounds that the body can use.

Body odor or body odour (BO) is present in all animals and its intensity can be influenced by many factors. Body odor has a strong genetic basis, but can also be strongly influenced by various factors, such as sex, diet, health, and medication. The body odor of human males plays an important role in human sexual attraction, as a powerful indicator of MHC/HLA heterozygosity. Significant evidence suggests that women are attracted to men whose body odor is different from theirs, indicating that they have immune genes that are different from their own, which may produce healthier offspring.

<span class="mw-page-title-main">Sweat gland</span> Small sweat-producing tubular skin structures

Sweat glands, also known as sudoriferous or sudoriparous glands, from Latin sudor 'sweat', are small tubular structures of the skin that produce sweat. Sweat glands are a type of exocrine gland, which are glands that produce and secrete substances onto an epithelial surface by way of a duct. There are two main types of sweat glands that differ in their structure, function, secretory product, mechanism of excretion, anatomic distribution, and distribution across species:

<span class="mw-page-title-main">Incretin</span> Group of gastrointestinal hormones

Incretins are a group of metabolic hormones that stimulate a decrease in blood glucose levels. Incretins are released after eating and augment the secretion of insulin released from pancreatic beta cells of the islets of Langerhans by a blood-glucose–dependent mechanism.

<span class="mw-page-title-main">H&E stain</span> Histological stain method

Hematoxylin and eosin stain is one of the principal tissue stains used in histology. It is the most widely used stain in medical diagnosis and is often the gold standard. For example, when a pathologist looks at a biopsy of a suspected cancer, the histological section is likely to be stained with H&E.

<span class="mw-page-title-main">Crop milk</span> Secretion used by some birds to feed their young

Crop milk is a secretion from the lining of the crop of parent birds in some species that is regurgitated to young birds. It is found among all pigeons and doves where it is also referred to as pigeon milk. Crop milk is also secreted from the crop of flamingos and the male emperor penguin, suggesting independent evolution of this trait. Unlike in mammals where only females produce milk, crop milk is produced by both males and females in pigeons and flamingos; and in penguins, only by the male. Lactation in birds is controlled by prolactin, which is the same hormone that causes lactation in mammals. Crop milk is a holocrine secretion, unlike in mammals where milk is an exocrine secretion. Crop milk contains both fat and protein, as with mammalian milk, but unlike mammalian milk, it contains no carbohydrates.

<span class="mw-page-title-main">Chromhidrosis</span> Medical condition

Chromhidrosis is a rare condition characterized by the secretion of colored sweat. It is caused by the deposition of lipofuscin in the sweat glands. Cases of red, blue, green, yellow, pink, and black sweat have been reported.

<span class="mw-page-title-main">Homogentisic acid</span> Chemical compound

Homogentisic acid is a phenolic acid usually found in Arbutus unedo (strawberry-tree) honey. It is also present in the bacterial plant pathogen Xanthomonas campestris pv. phaseoli as well as in the yeast Yarrowia lipolytica where it is associated with the production of brown pigments. It is oxidatively dimerised to form hipposudoric acid, one of the main constituents of the 'blood sweat' of hippopotamuses.

<span class="mw-page-title-main">Uropygial gland</span> Gland

The uropygial gland, informally known as the preen gland or the oil gland, is a bilobed sebaceous gland possessed by the majority of birds used to distribute the gland's oil through the plumage by means of preening. It is located dorsally at the base of the tail and is greatly variable in both shape and size. In some species, the opening of the gland has a small tuft of feathers to provide a wick for the preen oil. It is a holocrine gland enclosed in a connective tissue capsule made up of glandular acini that deposit their oil secretion into a common collector tube ending in a variable number of pores (openings), most typically two. Each lobe has a central cavity that collects the secretion from tubules arranged radially around the cavity. The gland secretion is conveyed to the surface via ducts that, in most species, open at the top of a papilla.

<span class="mw-page-title-main">Whippomorpha</span> Suborder of mammals

Whippomorpha or Cetancodonta is a group of artiodactyls that contains all living cetaceans and hippopotamuses. All Whippomorphs are descendants of the last common ancestor of Hippopotamus amphibius and Tursiops truncatus. This makes it a crown group. Whippomorpha is a suborder within the order Artiodactyla. The placement of Whippomorpha within Artiodactyla is a matter of some contention, as hippopotamuses were previously considered to be more closely related to Suidae (pigs) and Tayassuidae (peccaries). Most contemporary scientific phylogenetic and morphological research studies link hippopotamuses with cetaceans, and genetic evidence has overwhelmingly supported an evolutionary relationship between Hippopotamidae and Cetacea. Modern Whippomorphs all share a number of behavioural and physiological traits; such as a dense layer of subcutaneous fat and largely hairless bodies. They exhibit amphibious and aquatic behaviors and possess similar auditory structures.

<span class="mw-page-title-main">Malagasy hippopotamus</span> Extinct species of hippopotamus

Several species of Malagasy hippopotamus lived on the island of Madagascar but are now believed to be extinct. The animals were very similar to the extant hippopotamus and pygmy hippopotamus. The fossil record suggests that at least one species of hippopotamus lived until about 1,000 years ago and other evidence suggests that the species may have survived until much more recently. The taxonomy of these animals is not resolved and not widely studied.

<span class="mw-page-title-main">Cycloprop-2-ene carboxylic acid</span> Chemical compound

Cycloprop-2-ene carboxylic acid is a mycotoxin found in some mushrooms such as Russula subnigricans.

<span class="mw-page-title-main">Xylindein</span> Chemical compound

Xylindein is a quinone pigment, a dimeric naphthoquinone derivative. It is produced by fungi in the genus Chlorociboria. This pigment causes green staining of wood infected by the fungi.

Fungal isolates have been researched for decades. Because fungi often exist in thin mycelial monolayers, with no protective shell, immune system, and limited mobility, they have developed the ability to synthesize a variety of unusual compounds for survival. Researchers have discovered fungal isolates with anticancer, antimicrobial, immunomodulatory, and other bio-active properties. The first statins, β-Lactam antibiotics, as well as a few important antifungals, were discovered in fungi.

<span class="mw-page-title-main">Phagomimicry</span>

Phagomimicry is a defensive behaviour of sea hares, in which the animal ejects a mixture of chemicals, which mimic food, and overwhelm the senses of their predator, giving the sea hare a chance to escape. The typical defence response of the sea hare to a predator is to release two chemicals - ink from the ink gland and opaline from the opaline gland. While ink creates a dark, diffuse cloud in the water which disrupts the sensory perception of the predator by acting as a smokescreen and as a decoy, the opaline, which affects the senses dealing with feeding, causes the predator to instinctively attack the cloud of chemicals as if it were indeed food. This ink is able to mimic food by having a high concentration of amino acids and other compounds that are normally found in food, and the attack behaviour of the predator allows the sea-hares the opportunity to escape.

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. 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.
  4. "FACT CHECK: Is Hippopotamus Milk Pink?". Snopes.com. Retrieved 2022-02-16.