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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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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