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C3305

Sigma-Aldrich

Carbacyclin

≥90% (HPLC)

Synonym(s):

6a-Carba-prostaglandin I2, Carbocyclic PGI2

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About This Item

Empirical Formula (Hill Notation):
C21H34O4
CAS Number:
69552-46-1
Molecular Weight:
350.49
MDL number:
MFCD00210824
UNSPSC Code:
12352211
PubChem Substance ID:
24892602

Assay

≥90% (HPLC)

storage temp.

−20°C

SMILES string

[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(\C2)=C\CCCC(O)=O

InChI

1S/C21H34O4/c1-2-3-4-8-17(22)10-11-18-19-13-15(7-5-6-9-21(24)25)12-16(19)14-20(18)23/h7,10-11,16-20,22-23H,2-6,8-9,12-14H2,1H3,(H,24,25)/b11-10+,15-7+/t16-,17-,18+,19-,20+/m0/s1

InChI key

XZFRIPGNUQRGPI-WBQKLGIQSA-N

Gene Information

human ... PPARA(5465) , PPARD(5467) , PPARG(5468)

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
108K1386
120M1748
056K1562
036K1444
104H0870

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M J Mason et al.
The Journal of physiology, 533(Pt 1), 175-183 (2001-05-15)
Using simultaneous whole-cell patch-clamp and fluorescence measurements of [Ca2+]i in rat megakaryocytes we have investigated the requirement for functional inositol 1,4,5-trisphosphate (IP3) receptors in Ca2+ release induced by membrane depolarization during agonist stimulation. Voltage-dependent Ca2+ release was observed during application
Tadashi Kuroda et al.
Journal of molecular and cellular cardiology, 43(1), 54-62 (2007-06-02)
Prostacyclin (PGI2) and its analogues exert cardioprotective effects via the rhodopsin type membrane PGI2 receptor, IP. Peroxisome proliferator-activated receptor (PPAR) delta is a nuclear receptor abundantly expressed in cardiomyocytes and plays a pivotal role in maintaining constitutive mitochondrial fatty acid
K Noguchi et al.
Oral microbiology and immunology, 15(5), 299-304 (2001-01-12)
In the present study, we examined whether prostaglandin (PG) E2 and PGI2 regulated intercellular adhesion molecule-1 (ICAM-1) expression in human oral gingival epithelial cells stimulated with tumor necrosis factor alpha (TNF alpha). TNF alpha potently induced ICAM-1 expression in a
I Nagase et al.
FEBS letters, 494(3), 175-180 (2001-04-20)
Catecholamine-induced and beta-adrenergic receptor (beta-AR)-mediated thermogenesis in skeletal muscle is a significant component of whole-body energy expenditure. Skeletal muscle expresses uncoupling protein (UCP) 2 and UCP3, which can dissipate the transmitochondrial electrochemical gradient and thereby may be involved in regulation
Mikhail Kim et al.
The Journal of organic chemistry, 71(12), 4642-4650 (2006-06-06)
A fully stereocontrolled synthesis of 3-oxacarbacyclin (3) and a formal synthesis of carbacyclin (2) are described. The syntheses are based on the conjugate addition-azoalkene-asymmetric olefination strategy. Its key features are (1) the stereoselective establishment of the complete omega-side chain of
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