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Organic Halides in Nature

Page history last edited by Gina Lam 16 years, 7 months ago

 

 

 

 

 

Animals

 

     Sponges, corals and most seaweeds share an inability to avoid predators and parasites because they are anchored to the ocean floor. Lacking other means of defense, these organisms must rely on chemical warfare in order to survive and they do this through the production of halocarbon compounds. Among the sponge's weapons are several brominated dioxins and many metabolites(substances produced by metabolism) that prevent overgrowth by barnacles. These metabolites are used in solving a problem that continues to afflict ships, piers and almost every other man-made object in the ocean. In Hawaii, "swimmer's itch" is caused by a bromine-containing seaweed compound, and limu kohu contains at least 100 organohalogens, nearly all of which have previously unknown chemical structures.

 

 

  Marine species are the richest sources for organohalogens. The

    filamentous bluegreen algae Lyngbya (top left) synthesizes aplysiatoxin,

       the cause of "swimmer's itch". The sponge Dysidea dendyi produces

 several brominated dioxins; its close kin Dysidea granulosa is shown here

 (top right). Aplysia californica (middle) is a sea hare that emits ink

   derived from its algal diet-the same source for halogenated

 defensive compounds used by many other species of sea slugs.

The brilliantly colored nudibranch Chromodoris hamiltoni (bottom)

also creates its own chlorinated metabolites.

   

 

 

 

 

Dioxins are toxic compounds, but not all are made by human chemists. These three have very different sources: From left, spongiadioxin A from Dysidea dendyi; 1,3,6,8 tetrachlorodibenzo-p-dioxin (1,3,6,8-TCDD), a natural dioxin formed during the decay of plant matter in New Brunswick peat bogs; and 2,3,7,8 tetrachlorodibenzo-p-dioxin (2,3,7,8-TCDD), an industrial chemical.

  

     Nudibranchs and sea hares, two varieties of shell-less saltwater slugs,  depend on chemicals for survival in a world of predators. One species of sea hare secretes a bitter-tasting, bromine containing metabolite called panacene to discourage predators such as sharks. However, some nudibranchs lack the ability to produce panacene  and therefore must acquire it instead from their diet of sponges or algae. 

 

     The compound 2,6-dichlorophenol is made by female ticks as a sex pheromone. The German cockroach synthesizes two other chlorinated pheromones to induce aggregation (a group of organisms of the same or different species living closely together but less integrated than a society). And chloroform (which was used as an anesthetic during the mid-19th century and is now a common industrial solvent) has a number of natural sources. Termites, emit 15 percent of global atmospheric chloroform, perhaps as a waste product of the chloride compounds naturally present in wood. 

 

          

 

 

       The tiny poison-arrow frog Epipedo-bates  tricolor is a native of Ecuador that secretes epibatidine, a chlorine containing substance with a unique chemical structure .  The chemical's original purpose is to thwart potential predators.

 

 

 

      Our own species naturally produces the iodinated hormone thyroxine, which regulates basal metabolism and was thought for a hundred years to be the only organohalogen made by the human body. However, recent studies reveal that our bodies produce bleach (hypochlorous acid) and chlorine gas! White blood cells use chloride and the enzyme myeloperoxidase to kill microbial pathogens and perhaps tumor cells. Byproducts of these reactions include chlorinated proteins and nucleic acids. This chlorination process is an essential component of the immune system: Humans deficient in myeloperoxidase are highly susceptible to bacterial infections, particularly pneumonias. Of the few organobromines synthesized by human cells, a bromoester in cerebrospinal fluid, induces REM (rapid-eye-movement) sleep. 

 

 

 

 

  

Rocks and volcanoes

 

     Although living things overwhelmingly utilize organochlorines and organobromines in preference to other halocarbons, fluorine is actually the most abundant halogen in the Earth's crust: Volcanoes emit 11 million tons of hydrogen fluoride and 3 million tons of hydrogen chloride per year. Volcanoes on at least four continents (Asia, Europe, North and South America) emit these naturally formed organochlorine and organofluorine gases. Some of the resulting compounds are identical to some of the  CFCs that catalyze the breakdown of the ozone layer in the stratosphere.

 

 

 

 

 

     Rock also contains organohalogens, which can exist as pockets of gas or a component of certain minerals. When some rocks are crushed during mining, methyl chloride, dichloromethane, chloroform, carbon tetrachloride and other chlorinated chemicals are released. Potassium-salt mining releases thousands of tons of chloroform per year. One dark purple fluorite from Bavaria exudes the unmistakable smell of fluorine gas when crushed, earning it the name "stinkspat" among local miners. 

 

     Halogens aren't confined to terrestrial chemistry: Hydrogen chloride and hydrogen fluoride are also present in space, and at least four meteorites have contained chlorinated compounds.

 

  

 

 

 

 

Significant amounts of nonbiogenic organohalogens come from burning biomass. People set most fires; only 10 percent are caused by lightning or other natural sources. Together, these sources of biomass combustion release large quantities of methyl chloride (900,000 tons per year) and lesser amounts of methyl bromide (10,000 to 50,000 tons per year). The global input per year of atmospheric methyl chloride is estimated at 4 million tons. These figures dwarf the 10,000 tons per year coming from industry.

 

   

 

 

 

                                                                        

 

 


Pictures 
1] “Lyngbya, Dysidea granulose, Alplysia California, and Chromodoris hamiltoni.” AmericanScienctist.org 6 Mar. 2010.      <http://www.eurochlor.org/upload/documents/document68.pdf>.
2] “spongiadioxin A, 1,3,6,8-TCDD, and 2,3,7,8-TCDD.” AmericanScienctist.org 6 Mar. 2010.      <http://www.eurochlor.org/upload/documents/document68.pdf>.
4] “female%20lone%20star%20tick.” Co.monmouth.nj.us 6 Mar. 2010. <http://co.monmouth.nj.us/AgencyImages/61/female%20lone%20star%20tick.jpg>.
5] “epipedobates-anthonyi-1.” Aquaportail.com 6 Mar. 2010. <http://www.aquaportail.com/pictures0912/epipedobates-anthonyi-     1.jpg>.
6] “thyroxine.” embryology.med.unsw.edu.au 6 Mar. 2010. <http://embryology.med.unsw.edu.au/defect/images/thyroxine.jpg>.
7] “mayon_volcano05jpg.” arenal.net 6 Mar. 2010. <http://www.arenal.net/photo/gallery/arenal-volcano-daytime.jpg>.
8] “Bolton-meteorite.” boltonmuseums.org.uk 6 Mar. 2010. <http://www.boltonmuseums.org.uk/images/geologyimages/bolton-meteorite.jpg>.
9] “bonfire.” sacramentoscoop.com 6 Mar. 2010. <http://sacramentoscoop.com/wp-content/uploads/2008/10/bonfire.jpg>.

 

Comments (36)

Zeinab Ahmed said

at 8:43 pm on Mar 7, 2010

i think this one's nice

Mai Ghannam said

at 8:37 pm on Mar 7, 2010

this one?

Gina Lam said

at 8:35 pm on Mar 7, 2010

this one's distracting

Zeinab Ahmed said

at 8:33 pm on Mar 7, 2010

i like it.... lol i really like stripes

Mai Ghannam said

at 8:31 pm on Mar 7, 2010

this one makes the text stand out more

Zeinab Ahmed said

at 8:28 pm on Mar 7, 2010

they're pretty, but do they have to do with our project?

you know what'd be cool? if we could find one with the blue stripes, but no weird white part...

Zeinab Ahmed said

at 8:27 pm on Mar 7, 2010

ok never mind, you changed it

Mai Ghannam said

at 8:26 pm on Mar 7, 2010

check out the blue roses background, its pretier

Zeinab Ahmed said

at 8:26 pm on Mar 7, 2010

i love the blue stripes but the white part looks weird... for some odd reason it makes me feel claustrophobic....

Mai Ghannam said

at 8:18 pm on Mar 7, 2010

but i think we need something nicer, it kinda doesnt look that good

Zeinab Ahmed said

at 8:17 pm on Mar 7, 2010

nice!

Gina Lam said

at 3:58 pm on Mar 7, 2010

nevermind i'm being an idiot

Zeinab Ahmed said

at 11:23 am on Mar 7, 2010

okay, and anyways, comic sans matches the title thing

Mai Ghannam said

at 11:20 am on Mar 7, 2010

i think comic sans makes the text not boring anything formal like verdana will make them kinda too serious

Zeinab Ahmed said

at 11:16 am on Mar 7, 2010

i made the trihalomethanes page be in verdana. what do you think?

Zeinab Ahmed said

at 11:13 am on Mar 7, 2010

woa, there's like huge spaces between your paragraphs...

can we try verdana (wow i'm so demanding lol)?

Zeinab Ahmed said

at 11:09 am on Mar 7, 2010

maybe comic sans is better....

Zeinab Ahmed said

at 11:06 am on Mar 7, 2010

i don't really like comic sans, it makes me feel like the thing is a joke..... idk

or maybe arial would be nice

Zeinab Ahmed said

at 11:04 am on Mar 7, 2010

and how about using the font on the title page (i like it, it's pretty). except, i don't know what font it is, so we might have to kinda retype our info (which i actually don't mind doing)

Mai Ghannam said

at 11:03 am on Mar 7, 2010

oh and all of it should be comic sans font cuz i like that one

Mai Ghannam said

at 11:02 am on Mar 7, 2010

i think all of it should be black and a bit larger

Zeinab Ahmed said

at 11:01 am on Mar 7, 2010

one thing that we also have to do is make sure all our fonts are the same

Mai Ghannam said

at 11:00 am on Mar 7, 2010

i give up, i wish we hadn't deleted that page. it had the code on it. but the background right now matches our theme.

Farzana Afrin said

at 11:00 am on Mar 7, 2010

wow... gina stayed up till like four or five workin on this wiki
:0

Farzana Afrin said

at 10:57 am on Mar 7, 2010

lol then i guess ur the only one who considers urself that way :P

Mai Ghannam said

at 10:56 am on Mar 7, 2010

id like to consider myself as the better one :D

Farzana Afrin said

at 10:54 am on Mar 7, 2010

lol zeinab
great minds think alike
:)
too bad mai doesnt have our type of mind

Farzana Afrin said

at 10:53 am on Mar 7, 2010

maaaybe cause YOU DOOO !!!! lol joking

make ur words bigger... lol it always makes me feel like i wrote more if the words are bigger

Zeinab Ahmed said

at 10:53 am on Mar 7, 2010

they have loads of info

farzie, you missed the second half of our convo yesterday when i was talking about how i was tempted to steal the lock from mai

Mai Ghannam said

at 10:50 am on Mar 7, 2010

whatever i wouldnt lose anything important
why do my pages look like they have only a little bit of info?

Farzana Afrin said

at 10:49 am on Mar 7, 2010

i have a sudden urge to steal ur lock
lol
should i ? idk... im so tempted

Mai Ghannam said

at 10:49 am on Mar 7, 2010

trying to remember how to do the code for the background

Farzana Afrin said

at 10:48 am on Mar 7, 2010

watcha doin ?

Mai Ghannam said

at 10:47 am on Mar 7, 2010

hi farz

Farzana Afrin said

at 10:47 am on Mar 7, 2010

hi october :)

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