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Erythromycin

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Identification
Molecular formula
C37H67NO13
CAS number
114-07-8
IUPAC name
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
State
State

At room temperature, erythromycin is typically in a solid state as a crystalline powder.

Melting point (Celsius)
135.00
Melting point (Kelvin)
408.15
Boiling point (Celsius)
756.50
Boiling point (Kelvin)
1 029.70
General information
Molecular weight
733.94g/mol
Molar mass
733.9370g/mol
Density
1.1800g/cm3
Appearence

Erythromycin is a white or slightly yellow, crystalline powder. It is odorless or has a faint characteristic odor. The powder is sparingly soluble in water but more soluble in ethanol.

Comment on solubility

Solubility of (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione

The solubility of complex organic compounds like the one mentioned can vary significantly based on their structure and interactions with solvents. In general, the following factors influence solubility:

  • Functional Groups: The presence of polar groups such as hydroxyl (-OH) and amine (-NH2) can enhance solubility in polar solvents such as water.
  • Hydrophobic Regions: Conversely, large hydrophobic hydrocarbon sections can decrease solubility in polar solvents but may improve solubility in non-polar solvents.
  • Hydrogen Bonding: Compounds capable of extensive hydrogen bonding will often exhibit higher solubility in water.
  • Temperature Impact: Increasing temperature generally increases solubility for many solid solutes.

For this specific compound, with its multiple hydroxyl and dimethylamino substituents, we can expect:

  • A potential for increased solubility in polar solvents such as water or alcohols due to its hydroxyl groups.
  • Challenges regarding solubility in highly non-polar solvents because of its extensive hydrophobic hydrocarbon chains.
  • Variability in solubility based on specific pH levels and interactions with other chemical species in solution.

In summary, given the intricate structure of this compound, its solubility profile will likely be complex and largely dependent on the solvent environment as well as the concentration of the solute. Understanding these details is crucial for applications in pharmaceuticals and organic synthesis.

Interesting facts

Interesting Facts about the Compound

This compound is a complex organic molecule, renowned for its intricate arrangement of stereocenters and functional groups. Its structural features imbue it with fascinating properties and potential applications in various fields of science, particularly in medicinal chemistry.

Key Features

  • Stereochemistry: This compound exhibits multiple chiral centers, which allow for a range of stereoisomers. Chirality plays a critical role in how compounds interact with biological systems, affecting their efficacy and safety.
  • Functional Groups: The presence of hydroxyl groups contributes to its potential hydrogen-bonding abilities, aiding in its solubility and interaction with biological macromolecules.
  • Natural Product Inspiration: Many complex organic compounds are derived from natural sources. This compound's structural features resemble those found in certain natural products that exhibit significant pharmacological activities.

Potential Applications

  • Pharmaceutical Development: Given its elaborate structure, this compound could serve as a scaffold for designing new drugs. Chemists often modify specific parts of such structures to enhance biological activity or reduce side effects.
  • Research Tool: Compounds with unique stereochemistry are invaluable in research as they can serve as probes to study biochemical pathways and interactions.
  • Industrial Uses: Beyond medicinal roles, the intricate structure may find uses in materials science, particularly in developing polymers or as catalysts in chemical reactions.

In conclusion, this compound embodies the complexity and beauty of organic chemistry. Its synthesis and study not only deepen our understanding of molecular interactions but also pave the way for innovations in health and technology. As one prominent chemist once said, "The essence of chemistry lies not just in understanding matter, but in transforming it to improve our world."

Synonyms
erythromycin
114-07-8
Erythromycin A
E-Mycin
Abomacetin
Erythromycinum
Emgel
Eritromicina
Erythromycine
Robimycin
Torlamicina
Eryderm
Erythro-Statin
Erythromycin base
E-Glades
Ery-Tab
Pantomicina
Erygel
Sansac
E-Base
Erythra-Derm
ERYC
Dumotrycin
Mephamycin
Ermycin
Eryacne
Stiemycin
Aknin
Erycen
Wemid
R-P Mycin
Eryc Sprinkles
Theramycin Z
E-Solve 2
Ak-Mycin
Erythromast 36
Erytrociclin
Acneryne
Endoeritrin
Eritomicina
Eryacnen
Erydermer
Eryhexal
Erythroderm
Iloticina
Latotryd
Lederpax
Oftamolets
Pantoderm
Pantodrin
Pharyngocin
Primacine
Proterytrin
Stiemicyn
Tiprocin
Acnesol
Derimer
Deripil
Emuvin
Emycin
Erecin
Erisone
Erymed
Erysafe
Erytab
Erytop
Inderm
Mercina
Romycin
AustriaS
Eros
C-Solve-2
Ery-maxin
Erythro-Teva
Sans-acne
Erimycin-T
Ery-Diolan
Inderm Gel
Del-Mycin
Udima Ery Gel
Aknederm Ery Gel
Abboticin
Emu-Ve
Akne Cordes Losung
Eryc 125
Ilotycin T.S.
Skid Gel E
E-Mycin (base)
Emu-V
Ery-B
Ery-Tab (base)
E-Base (base)
ERYC (base)
erythromycin-A
A/T/S
Erythrogran
Erythroguent
Erythromid
Propiocine
Dotycin
Erycinum
Ilocaps
PCE Dispertab (base)
Erycin
Kesso-Mycin
Eryc-125
Eryc-250
Taimoxin-F
Oftalmolosa Cusi Eritromicina
Staticin
Retcin
erthromycin
Sentry AQ mardel maracyn
Eritromicina [INN-Spanish]
Erythromycine [INN-French]
Erythromycinum [INN-Latin]
CCRIS 9078
DTXSID4022991
UNII-63937KV33D
CHEBI:42355
HSDB 3074
EM-A
EINECS 204-040-1
NSC 55929
NSC-55929
PCE (ERYTHROMYCIN)
63937KV33D
AI3-50138
DTXCID102991
EC 204-040-1
Erythromycin [USP:INN:BAN:JAN]
NSC55929
ERY
BENZAMYCIN COMPONENT ERYTHROMYCIN
Eritromicina (INN-Spanish)
Erythromycine (INN-French)
Erythromycinum (INN-Latin)
ERYTHROMYCIN (MART.)
ERYTHROMYCIN [MART.]
ERYTHROMYCIN (USP-RS)
ERYTHROMYCIN [USP-RS]
ERYTHROMYCIN (EP MONOGRAPH)
Erythromycin (USP:INN:BAN:JAN)
ERYTHROMYCIN [EP MONOGRAPH]
ERYTHROMYCIN (USP MONOGRAPH)
ERYTHROMYCIN [USP MONOGRAPH]
Spotex
ErythromycinBase
Gallimycin-36
ErythromycinBase Filmtab
Erythro-100 Injection
API E.M. Erythromycin
Erythromycin Base Filmtab
Erythro-36, Erythro-Dry
API E.M ERYTHROMYCIN
CHEBI:48923
Gallimycin Injection, Gallimycin-100
ERYTHROMYCIN COMPONENT OF BENZAMYCIN
204-040-1
rp-mycin
Erymax
Ilotycin
Erythrocin
Erycette
Akne-Mycin
T-Stat
erythro
Eritrocina
MFCD00084654
Benzamycin
CHEMBL532
J01FA01
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
Erythromycin C-13
Aknemycin
8HPH7ND0LN
(3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)-4-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)oxacyclotetradecane-2,10-dione
[3R-(3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)]-4-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl]oxy]oxacyclotetradecane-2,10-dione
Ilosone (estolate)
N-Methylerythromycin A
Erythromycin, labeled with carbon-13
Staticin (TN)
Akne-mycin (TN)
Erygel (TN)
Eryc (TN)
T-stat (TN)
Pce (TN)
SR-05000001618
Erythromycin & VRC3375
82343-12-2
NCGC00094670-01
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
CAS-114-07-8
Prestwick_205
215031-94-0
Spectrum_000115
Spectrum_000659
Prestwick3_000151
Spectrum2_000759
Spectrum2_001263
Spectrum4_000538
Spectrum5_001596
UNII-8HPH7ND0LN
ERYTHROMYCIN [MI]
E0751
Erythromycin A, B + C
ERYTHROMYCIN [INN]
ERYTHROMYCIN [JAN]
ERYTHROMYCIN [HSDB]
SCHEMBL2601
ERYTHROMYCIN [VANDF]
BSPBio_000282
BSPBio_002480
KBioGR_001175
KBioSS_000555
KBioSS_001139
MLS001066618
BIDD:GT0017
DivK1c_000294
DivK1c_000397
DivK1c_000702
ERYTHROMYCIN [WHO-DD]
ERYTHROMYCIN [WHO-IP]
SPECTRUM1500280
SPBio_000778
SPBio_001226
E-Base;E-Mycin;Erytromycin A
BPBio1_000312
GTPL1456
Erythromycin (JP18/USP/INN)
HMS500O16
KBio1_000294
KBio1_000397
KBio1_000702
KBio2_000555
KBio2_001139
KBio2_003123
KBio2_003707
KBio2_005691
KBio2_006275
ERYTHROMYCIN [GREEN BOOK]
MSK7801
NINDS_000294
NINDS_000397
NINDS_000702
ERYTHROMYCIN [ORANGE BOOK]
HMS1920M04
HMS2091D05
HMS2095O04
HMS3712O04
Pharmakon1600-01500280
HY-B0220
RKL10096
Tox21_111311
Tox21_111869
Tox21_300515
BDBM50344942
CCG-38992
LMPK04000006
NSC756759
ERYTHROMYCINUM [WHO-IP LATIN]
AKOS015895249
AE22796
DB00199
NSC-756759
IDI1_000294
IDI1_000397
IDI1_000702
SMP1_000119
NCGC00179619-01
NCGC00179619-02
NCGC00179619-03
NCGC00254234-01
AC-12744
AC-12901
SMR000544946
Erythromycin, potency: >=850 mug per mg
Erythromycin, tested according to Ph.Eur.
SBI-0051368.P003
Erythromycin, N-demethyl-N-(methyl-11C)-
Erythromycin 1000 microg/mL in Acetonitrile
NS00000203
Erythromycin, meets USP testing specifications
C01912
D00140
AB00051981_09
AB00051981_10
Erythromycin, Biotechnology Performance Certified
Erythromycin estolate impurity, free erythromycin-
Q213511
SR-01000799155
Erythromycin, BioReagent, suitable for cell culture
SR-01000799155-2
SR-05000001618-1
SR-05000001618-2
BRD-K63550407-001-12-7
BRD-K63550407-001-13-5
BRD-K63550407-028-03-9
BRD-K63550407-028-04-7
Z2587996953
Erythromycin A, European Pharmacopoeia (EP) Reference Standard
Erythromycin, United States Pharmacopeia (USP) Reference Standard
ERYTHROMYCIN ESTOLATE IMPURITY, FREE ERYTHROMYCIN [EP IMPURITY]
ERYTHROMYCIN ESTOLATE IMPURITY, FREE ERYTHROMYCIN- [USP IMPURITY]
Erythromycin, for microbiological assay, European Pharmacopoeia (EP) Reference Standard
Erythromycin, Pharmaceutical Secondary Standard; Certified Reference Material
(3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)-4-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-(2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyloxy)-14-ethyl-7,12,13-trihydroxy-6-[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (non-preferred name)
[3R-(3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)]-4-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-|A-L-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-|A-D-xylo-hexopyranosyl]oxy]oxacyclotetradecane-2,10-dione
7540-22-9