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Thyroxine

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Identification
Molecular formula
C15H11I4NO4
CAS number
7488-70-2
IUPAC name
(2S)-2-amino-3-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]propanoic acid
State
State

Thyroxine is in a solid state at room temperature. Typically, it is handled in the form of a salt, such as levothyroxine sodium, for pharmaceutical use in various health applications.

Melting point (Celsius)
231.00
Melting point (Kelvin)
504.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
776.87g/mol
Molar mass
776.8650g/mol
Density
1.3000g/cm3
Appearence

Thyroxine appears as an off-white or pale brown, odorless crystalline powder. Due to its light sensitivity, it should be kept in a tightly sealed container and protected from light. Over time or with improper storage, it may darken upon exposure to air and moisture.

Comment on solubility

Solubility of (2S)-2-amino-3-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]propanoic acid

The solubility of (2S)-2-amino-3-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]propanoic acid, with the formula C15H11I4NO4, can be influenced by several factors due to its complex structure. Generally, the presence of multiple iodine atoms in its structure hints at significant hydrophobic characteristics which may decrease overall solubility in water.

Factors Influencing Solubility:

  • Polarity: The compound contains both polar and non-polar regions, which creates a challenge for solubility in polar solvents like water.
  • Hydrogen Bonding: The hydroxyl (-OH) group contributes to the potential for hydrogen bonding, enhancing solubility in polar solvents to some extent.
  • Iodine Content: With four iodine atoms, its hydrophobic nature is pronounced, making it less likely to dissolve in aqueous solutions.
  • pH Effects: The carboxylic acid (-COOH) group may ionize under basic conditions, potentially increasing solubility in alkaline solutions.

In summary, while there are factors that could promote some level of solubility in specific conditions, the overall expectation is that solubility in water may be limited due to the compound's high iodine content. As the saying goes, "like dissolves like", and in this case, the balance of polar and non-polar interactions will significantly dictate solubility behaviors.

Interesting facts

Interesting Facts about (2S)-2-amino-3-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]propanoic acid

(2S)-2-amino-3-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]propanoic acid, commonly known for its complex structure and notable features, is a fascinating compound in the realm of organic chemistry. Here are some intriguing aspects:

  • Multi-functional Roles: This compound has significant biological implications, often studied for its potential role in pharmaceuticals, especially in drug design targeting specific pathways.
  • Halogen Diversity: The presence of multiple iodine atoms in its structure enhances its reactivity and can lead to unique properties, making it a subject of interest in medicinal chemistry.
  • Phenolic Influence: The hydroxyl group of the phenol moiety contributes to its potential as an antioxidant. Compounds with phenolic structures are frequently investigated for their health benefits.
  • Chirality Matters: The chiral center in this compound implies that it can exist in enantiomeric forms, which may lead to different biological activities, thus highlighting the importance of stereochemistry in medicinal applications.
  • Research Opportunities: Due to its complex structure, this compound presents numerous research avenues, from synthesis challenges to exploring its pharmacokinetics and pharmacodynamics.

In the words of a renowned chemist, "The smallest change in molecular structure can lead to vastly different interactions and functions." This compound exemplifies that notion beautifully, embodying a rich tapestry of chemistry waiting to be unraveled.

As a student or researcher delving into the world of organic compounds, studying such complex molecules not only sharpens your understanding of structural chemistry but also ignites your curiosity about their real-world applications.

Synonyms
liothyronine
triiodothyronine
3,3',5-Triiodo-L-thyronine
6893-02-3
Liothyronin
Tresitope
3,5,3'-triiodothyronine
Liotironina
T3
triothyrone
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine
Liothyroninum
3,5,3'-Triiodo-L-thyronine
L-Liothyronine
Lyothyronine
Cyronine
L-T3
3,3',5-Triiodothyronine
3,5,3'TRIIODOTHYRONINE
L-3,3',5-TriioDOThyronine
L-triiodothyronine
(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid
Rathyronine, (s)-
L-3,5,3'-Triiodothyronine
CHEBI:18258
(S)-2-amino-3-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)propanoic acid
Liotironina [INN-Spanish]
Triiodo-L-thyronine
L-Tyrosine, O-(4-hydroxy-3-iodophenyl)-3,5-diiodo-
Liothyronine (GMP)
Liothyronine (INN)
06LU7C9H1V
DTXSID8023216
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine
HSDB 3110
EINECS 229-999-3
MFCD00002593
NSC 80203
NSC-80203
Thyronine, 3,3',5-triiodo-, L-
Liothyroninum [INN-Latin]
BRN 2710227
CHEMBL1544
UNII-06LU7C9H1V
4-(3-Iodo-4-hydroxyphenoxy)-3,5-diiodophenylalanine
4-(4-hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine
DTXCID403216
3,5,3'-triiodothyronine, l-
Alanine, 3-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-, L-
LIOTHYRONINE [INN]
Liothyroninum (INN-Latin)
Liotironina (INN-Spanish)
T-3
LIOTHYRONINE (USP-RS)
LIOTHYRONINE [USP-RS]
T3 (amino acid)
LIOTHYRONINE (USP IMPURITY)
LIOTHYRONINE [USP IMPURITY]
Liothyronine [INN:BAN]
(+)-Triiodothyronine
CAS-6893-02-3
T3 (VAN)
Triiodothyronine, l-
3,5,3'-Tri-iodo-L-thyronine
Triiodothyronine (T3)
SR-05000000455
NSC80203
NSC-46046
Therapeutic T3
3,3',5-Triiodothyronine, L-
4-(3-iodo-4-hydroxy-phenoxy)-3,5-diiodophenylalanine
1xzx
(2S)-2-AMINO-3-(4-(4-HYDROXY-3-IODOPHENOXY)-3,5-DIIODOPHENYL)PROPANOIC ACID
Prestwick_135
Spectrum_001445
L-3-(4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl)alanine
Triiodothyronine;3,3',5-Triiodo-L-thyronine;T3
Liothyronine (Standard)
Prestwick0_000853
Prestwick1_000853
Prestwick2_000853
Prestwick3_000853
Spectrum2_001984
Spectrum3_001887
Spectrum4_000326
Spectrum5_001793
LIOTHYRONINE [MI]
Epitope ID:131324
LIOTHYRONINE [HSDB]
SCHEMBL8300
NCIStruc1_000449
LIOTHYRONINE [VANDF]
REGID_for_CID_5920
BSPBio_000865
BSPBio_003394
KBioGR_000671
KBioGR_002568
KBioSS_001925
KBioSS_002577
MLS000028458
O-(4-Hydroxy-3-iodophenyl-3,5-diiodo-L-tyrosine
3,5,3'-triodo-L-thyronine
LIOTHYRONINE [WHO-DD]
SPBio_002167
SPBio_002786
BPBio1_000953
GTPL2634
HY-A0070AG
HY-A0070AR
L-3,3',5-triiodo-Thyronine
BCBcMAP01_000192
BDBM18860
HY-A0070A
KBio2_001925
KBio2_002568
KBio2_004493
KBio2_005136
KBio2_007061
KBio2_007704
KBio3_002897
KBio3_003046
H03AA02
cMAP_000088
HMS1570L07
HMS2097L07
HMS2235A22
HMS3714L07
TRIIODOTHYRONINE (T3 OR LIOTHYRONINE, ACTIVE) (6-11%)
Tox21_110029
Tox21_301943
HB7470
NCGC00013556
s5726
3,5,3'-triiodo-L-thyronine (T3)
(S)-2-Amino-3-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)propanoicacid
AKOS016003266
3,3',5-Triiodo-L-thyronine, 95%
CCG-220853
CS-4141
DB00279
FT28506
L-3,3',5-Triiodothyronine, free acid
SMP1_000179
NCGC00013556-01
NCGC00013556-02
NCGC00013556-03
NCGC00013556-04
NCGC00013556-05
NCGC00013556-12
NCGC00013556-15
NCGC00096669-01
NCGC00096669-02
NCGC00255336-01
[125I]T3
AC-31935
AS-17446
SMR000058402
SBI-0206718.P001
DB-021796
CS-0622788
NS00076841
T0453
A11632
C02465
D08128
EN300-123970
Q327362
SR-01000003143
SR-01000003143-4
SR-05000000455-2
SR-05000000455-3
BRD-K89152108-001-03-3
BRD-K89152108-236-05-0
BRD-K89152108-236-06-8
BRD-K89152108-236-07-6
LEVOTHYROXINE SODIUM IMPURITY A [EP IMPURITY]
3,3',5-Triiodo-L-thyronine, >=95% (HPLC), powder
Z1557400301
D-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]alanine
L-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-Alanine
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine;Liothyronine
Liothyronine, United States Pharmacopeia (USP) Reference Standard
3,3',5 Triiodothyronine (T3), IRMM(R) certified Reference Material
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine,labeled with(125i)iodine
Liothyronine, Pharmaceutical Secondary Standard; Certified Reference Material
229-999-3