1,2,3,4,5-Cyclopentanepentol, also named cyclopentane-1,2,3,4,5-pentol or 1,2,3,4,5-pentahydroxycyclopentane is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with formula or , whose

molecule A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioch ...

consists of a ring of five

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...

atoms (a

cyclopentane Cyclopentane (also called C pentane) is a highly flammable alicyclic hydrocarbon with chemical formula C5H10 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It occur ...

skeleton), each connected to one

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...

and one

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

group A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic iden ...

. The unqualified term "cyclopentanepentol" usually refers to this compound. There are four distinct

stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...

s with this same structure. The compound is a five-fold

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

of cyclopentane, and technically a cyclic

sugar alcohol Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing one hydroxyl group (–OH) attached to each carbon atom. They are white, water-soluble solids ...

cyclitol In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is or where 3 ≤ ''x'' ≤ ''n''. The name is also used for c ...

). However it is very rarely found in nature, and therefore it has received much less attention than the ubiquitous six-carbon version,

inositol Inositol, or more precisely ''myo''-inositol, is a carbocyclic sugar that is abundant in the brain and other mammalian tissues; it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and ...

Isomers

There are four distinct stereoisomers of cyclopentane-1,2,3,4,5-pentol, distinguished by the position of the hydroxyls relative to the mean plane of the ring. All have a plane of symmetry, and therefore are not chiral. One naming convention for the isomers labels each carbon number 1-5 with "α" for the side of the ring plane with most hydroxyls (three or more), and "β" for the other side. Another convention lists the hydroxyls on the majority side and then those on the minority side, with the two groups separated by a slash (and a "0" is written when the second list would be empty). The four possible isomers are: * 1α,2α,3α,4α,5α, 1,2,3,4,5/0, or all-''cis'' (all hydroxyls on the same side). CAS 34322-89-9. Long needles, melting point 283 °C (darkens ar 220 °C). Obtained from cyclopentane-1α,2α-epoxi-3α,4α,5α-triol by treatment with

hydrogen bromide Hydrogen bromide is the inorganic compound with the formula . It is a hydrogen halide consisting of hydrogen and bromine. A colorless gas, it dissolves in water, forming hydrobromic acid, which is saturated at 68.85% HBr by weight at room temper ...

to obtain cyclopentane-1β-bromo-2α,3α,4α,5α-tetrol, followed by

benzoyl In organic chemistry, benzoyl (, ) is the functional group with the formula C6H5CO-. It can be viewed as benzaldehyde missing one hydrogen. The term "benzoyl" should not be confused with benzyl, which has the formula C6H5CH2. The benzoyl group ...

ation and treatment with

DMSO Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds an ...

and

sodium bicarbonate Sodium bicarbonate (IUPAC name: sodium hydrogencarbonate), commonly known as baking soda or bicarbonate of soda, is a chemical compound with the formula NaHCO3. It is a salt composed of a sodium cation ( Na+) and a bicarbonate anion ( HCO3−) ...

. * 1α,2α,3α,4α,5β or 1,2,3,4/5. CAS 18939-02-1. Soluble in hot

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...

. Melting point 220 °C or 209-210 °C. Obtained by

solvolysis In chemistry, solvolysis is a type of nucleophilic substitution (S1/S2) or elimination where the nucleophile is a solvent molecule. Characteristic of S1 reactions, solvolysis of a chiral reactant affords the racemate. Sometimes however, the ster ...

of two tetra-O-acetyl-O-

tosyl In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos) is a univalent functional group with the chemical formula –. It consists of a tolyl group, –, joined to a sulfonyl group, ––, with the open valence on s ...

-cyclopentanepentol, and also by hydroxylation of 3,4,5-trihydroxy-1-cyclopentenes. * 1α,2α,3α,4β,5β or 1,2,3/4,5. CAS 18939-07-6. Soluble in ethanol. Melting point 168-169 °C, or 176 °C. Obtained by deamination of (1,4/2,3,5)-5-amino-1,3-di-O-acetyl-2,3-O-cyclohexylidene-l,2,3,4-cycopentanetetrol, and also by hydroxylation of 3,4,5-trihydroxy-1-cyclopentenes. * 1α,2α,3β,4α,5β or 1,2,4/3,5. CAS 57784-52-8. Melting point 149.5-150.5 °C. Obtained from cyclopent-4-ene-1,3/2-trio1 by

epoxidation In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for ...

and subsequent

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

; also by acid hydrolysis of an anhydro-cyclopentanepentol, DL-1,2-anhydro-4,5-O-cyclohexylidene-1,2,3/4,5-cyclopentanepentol; and also from a D-''xylo''-pento dialdose. The last three isomers interconvert by heating them at about 104 °C with 95%

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...

in the presence of a

strong acid Acid strength is the tendency of an acid, symbolised by the chemical formula HA, to dissociate into a proton, H+, and an anion, A-. The dissociation of a strong acid in solution is effectively complete, except in its most concentrated solutions. ...

. The conversion between 1,2,3,4/5 and 1,2,3/4,5 is faster and entails the hydrogen and hydroxyl switching places on either of the two carbon atoms located between an "α" and a "β" position. The formation of 1,2,4/3,5 is much slower and equilibrium is reached only after many days. The relative stabilities are 1,2,4/3,5 > 1,2,3/4,5 > 1,2,3,4/5, with equilibrium ratios 72 : 17.5 : 10.5. The isomers can be identified qualitatively by their mobility in paper ionophoresis in a solution of

calcium acetate Calcium acetate is a chemical compound which is a calcium salt of acetic acid. It has the formula Ca(C2H3O2)2. Its standard name is calcium acetate, while calcium ethanoate is the systematic name. An older name is acetate of lime. The anhydrous ...

and

, and revealed with a

manganese sulfate Manganese(II) sulfate usually refers to the inorganic compound with the formula MnSO4·H2O. This pale pink deliquescent solid is a commercially significant manganese(II) salt. Approximately 260,000 tonnes of manganese(II) sulfate were produced w ...

potassium permanganate Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, that dissolves in water as K+ and , an intensely pink to purple solution. Potassium permanganate is widely used in the c ...

reagent. The mobilities of the isomers, relative to that of ''cis''-inositol, are 0.95 (12345/0), 0.44 (1234/5), 0.18 (123/45), and 0.04 (124/35). The variation is attributed to the formation of

chelate Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...

s with the

calcium Calcium is a chemical element with the symbol Ca and atomic number 20. As an alkaline earth metal, calcium is a reactive metal that forms a dark oxide-nitride layer when exposed to air. Its physical and chemical properties are most similar to ...

cation An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...

s, with varying strengths depending on the number of hydroxyl pairs that can bind to the cation. Similar results can be obtained with

lanthanum Lanthanum is a chemical element with the symbol La and atomic number 57. It is a soft, ductile, silvery-white metal that tarnishes slowly when exposed to air. It is the eponym of the lanthanide series, a group of 15 similar elements between lantha ...

cations and

thin-layer chromatography Thin-layer chromatography (TLC) is a chromatography technique used to separate non-volatile mixtures. Thin-layer chromatography is performed on a sheet of an inert substrate such as glass, plastic, or aluminium foil, which is coated with a t ...

Mass spectrometry Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is use ...

of the compound generates mainly the ion HO–CH=CH=CH=O⁺H (mass-charge ratio 73) and a neutral radical ^•.

Derivatives

Many

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

s are known, such as penta

s and penta

acetyl In organic chemistry, acetyl is a functional group with the chemical formula and the structure . It is sometimes represented by the symbol Ac (not to be confused with the element actinium). In IUPAC nomenclature, acetyl is called ethanoyl, ...

s. Trteatment of the derivative 3,4,5-tri-O-acetyl-1,2-O-ethylidene-(1,2,4/3,5)-cyclopentanepentol with

triphenylcarbenium In chemistry, triphenylcarbenium, triphenylmethyl cation, tritylium , or trityl cation is an ion with formula or , consisting of a carbon atom with a positive charge connected to three phenyl groups. It is a charged version of the triphenylmeth ...

tetrafluoroborate Tetrafluoroborate is the anion . This tetrahedral species is isoelectronic with tetrafluoroberyllate (), tetrafluoromethane (CF4), and tetrafluoroammonium () and is valence isoelectronic with many stable and important species including the perchl ...

to yield the cation 3,4,5-tri-O-acetyl-(1,2,4/3,5)-cyclopentanepentol-1,2-O-acetoxonium, which exhibits a peculiar 10-stage cyclic rearrangement. Cyclopentanepentols form dihydrogen

phosphate In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthophosphoric acid . The phosphate or orthophosphate ion is derived from phospho ...

esters analogous to inositol's

phytic acid Phytic acid is a six-fold dihydrogenphosphate ester of inositol (specifically, of the ''myo'' isomer), also called inositol hexakisphosphate (IP6) or inositol polyphosphate. At physiological pH, the phosphates are partially ionized, resulting ...

esters. The related compound 1,2,3,4,5-pentakis(hydroxymethyl)-cyclopentane (a colourless viscous oil, soluble in ''tert''-butanol and

) was synthesized in 1985 by L. M. Tolbert and others. It was hoped that dehydrative

dimer Dimer may refer to: * Dimer (chemistry), a chemical structure formed from two similar sub-units ** Protein dimer, a protein quaternary structure ** d-dimer * Dimer model, an item in statistical mechanics, based on ''domino tiling'' * Julius Dimer ...

ization of this product would yield

dodecahedrane Dodecahedrane is a chemical compound, a hydrocarbon with formula , whose carbon atoms are arranged as the vertices (corners) of a regular dodecahedron. Each carbon is bound to three neighbouring carbon atoms and to a hydrogen atom. This compound ...

Natural occurrence

Organic compounds similar to (and possibly mimicking) glycoglycerolipids, with a 1,2,4/3,5-cyclopentanepentol group connected to the

glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...

core in place of the

sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or double ...

group, have been found in several genera of marine

sponge Sponges, the members of the phylum Porifera (; meaning 'pore bearer'), are a basal animal clade as a sister of the diploblasts. They are multicellular organisms that have bodies full of pores and channels allowing water to circulate through t ...

s with widely separate ranges. Calditol is a substance found in the

archaeobacteria Archaea ( ; singular archaeon ) is a domain of single-celled organisms. These microorganisms lack cell nuclei and are therefore prokaryotes. Archaea were initially classified as bacteria, receiving the name archaebacteria (in the Archaebact ...

of the order ''

Sulfolobales In taxonomy, the Sulfolobales are an order of the Thermoprotei. Phylogeny The currently accepted taxonomy is based on the List of Prokaryotic names with Standing in Nomenclature (LPSN) and National Center for Biotechnology Information (NCBI) ...

''. It is an

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

that can be viewed as the condensation of

and 3α-hydroxymethyl-1α,2α,3β,4α,5β-hydroxy cyclopentane, forming an ether bridge –O– between the 1-carbon of the former and the 4-carbon of the latter. Its seems to protects the cells in acidic environments. Trace amounts of cyclopentanepentol were identified in some plants, such as the red flower calyces of ''

Hibiscus sabdariffa Roselle (''Hibiscus sabdariffa'') is a species of flowering plant in the genus ''Hibiscus'' that is native to Africa, most likely West Africa and also found in India especially Maharashtra with local name ambali. In the 16th and early 17th cent ...

'' (roselle); the plant ''

Maclura pomifera ''Maclura pomifera'', commonly known as the Osage orange ( ), is a small deciduous tree or large shrub, native to the south-central United States. It typically grows about tall. The distinctive fruit, a multiple fruit, is roughly spherical, b ...

'' (Osage orange); and the

cyanobacterium Cyanobacteria (), also known as Cyanophyta, are a phylum of gram-negative bacteria that obtain energy via photosynthesis. The name ''cyanobacteria'' refers to their color (), which similarly forms the basis of cyanobacteria's common name, blue ...

'' Oscillatoria willei'' as well as in the products of its hydropyrolysis.

History

The 1,2,4/3,5 isomer was briefly described in 1963 by H. Z. Sable and others. In 1968, Th. Posternak reported observation of 1,2,3,4/5 and 1,2,3/4,5, without the synthesis method. Better synthesis methods for these three were published by S. J. Angyal and B. M. Luttrell in 1970. Alternative methods for 1,2,3,4/5 and 1,2,3/4,5 were published in the same year by G. Wolczunowicz and others. The remaining all-''cis'' isomer (1,2,3,4,5/0) was synthesized in 1971 by F. G. Cocu and Posternak.

References

(2019
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Phytochemical Analysis and Medecinal Evaluation of Hydro Ethanolic Extract of Two Varieties ''Hibiscus sabdariffa'' Calyxes
. ''International Journal of Green and Herbal Chemistry'', Green Chemistry series, volume 5, issue 3, pages 349-354. Barry V. L. Potter (1998) "Structure-Activity Relationships of Adenophostin A and Related Molecules at the 1-D-myo-Inositol 1,4,5-Trisphosphate Receptor". ''American Chemical Society Symposium Series'', volume 718, chaper 10, pages 158-179 Antony V.Samrot and T.Thirunalasundari (2012): "[wprim.whocc.org.cn/admin/article/downloadAppendix?article=/upload/articleFile/P020160926333045048197.pdf&articleId=625657 Effect of ''Oscillatoria willei'' – a marine cyanobacterium on hydrazine induced toxicity]". ''Malaysian Journal of Microbiology'', volume 8, issue 4, pages 229-234. V. V. Platonov, A. A. Khadartsev L. N. Belozerova (2017):
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("Chromato-Mass-Spectrometry of Alcohol Extraction of ''Maclura''"). ''Вестник новых медицинских технологий'' (''Journal of New Medical Technologies''), electronic edition, volume 2017, issue 2. UDC: 581.1 William W. Christie (2019):

. Article on th

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Isomers

Derivatives

Natural occurrence

History

See also

References