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{{orphan|date=December 2009}}

{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 399503456
| Watchedfields = changed
⚫ |ImageFile=Ambrein.svg
⚫ | verifiedrevid = 419851613
⚫ |ImageSize=160
⚫ | ImageFile = Ambrein.svg
⚫ |IUPACName=(1R,2R,8aS)-1--4-methylhex-3-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
⚫ | ImageSize = 160
⚫ |OtherNames=Ambrein
⚫ | IUPACName = (1''R'',2''R'',4a''S'',8a''S'')-1-<nowiki/>{(3''E'')-6--4-methylhex-3-en-1-yl}-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
⚫ | OtherNames = Ambrein
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10000763 | ChemSpiderID = 10000763
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 78306
| InChI = 1/C30H52O/c1-22(15-16-24-23(2)13-10-18-27(24,3)4)12-9-14-26-29(7)20-11-19-28(5,6)25(29)17-21-30(26,8)31/h12,24-26,31H,2,9-11,13-21H2,1,3-8H3/b22-12+/t24-,25?,26-,29+,30-/m1/s1 | InChI = 1/C30H52O/c1-22(15-16-24-23(2)13-10-18-27(24,3)4)12-9-14-26-29(7)20-11-19-28(5,6)25(29)17-21-30(26,8)31/h12,24-26,31H,2,9-11,13-21H2,1,3-8H3/b22-12+/t24-,25?,26-,29+,30-/m1/s1
| InChIKey = BIADSXOKHZFLSN-CQDHYIGWBE | InChIKey = BIADSXOKHZFLSN-CQDHYIGWBE
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BIADSXOKHZFLSN-CQDHYIGWSA-N | StdInChIKey = BIADSXOKHZFLSN-CQDHYIGWSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=473-03-0 | CASNo = 473-03-0
⚫ | PubChem= 11826112
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | SMILES= C/C(=C\CC12(CCCC(C2CC1(C)O)(C)C)C)/CC3C(=C)CCCC3(C)C
| UNII = 1N9JB373FJ
⚫ | PubChem = 11826112
⚫ | SMILES = C/C(=C\CC12(CCCC(C2CC1(C)O)(C)C)C)/CC3C(=C)CCCC3(C)C
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| C=30 | H=52 | O=1 | C = 30 | H = 52 | O = 1
| Appearance= | Appearance =
| Density= | Density =
| MeltingPt= | MeltingPt =
| BoilingPt= | BoilingPt =
| Solubility= | Solubility =
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards =
| FlashPt= | FlashPt =
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
'''Ambrein''' is a fragrant substance that is used in the perfume industry. It is the chief constituent of ], a secretion from the digestive system of the ], and has been suggested as the possible active component producing the supposed ] effects of ambergris.<ref>Sandroni P. Aphrodisiacs past and present: a historical review. ''Clinical Autonomic Research''. 2001 Oct;11(5):303-7. {{DOI|10.1007/BF02332975}} PMID 11758796</ref> '''Ambrein''' is a ] alcohol that is the chief constituent of ], a secretion from the digestive system of the ]. It has been suggested as the possible active component producing the supposed ] effects of ambergris.<ref>{{cite journal | vauthors = Sandroni P | title = Aphrodisiacs past and present: a historical review | journal = Clinical Autonomic Research | volume = 11 | issue = 5 | pages = 303–7 | date = October 2001 | pmid = 11758796 | doi = 10.1007/BF02332975 | s2cid = 40455528 }}</ref> Although ambrein itself is odorless, it serves as the biological precursor for aromatic derivatives such as ] and is thought to possess fixative properties for other odorants.


⚫ It has been shown to act as an ]<ref>{{cite journal | vauthors = Taha SA | title = Studies on the mode of action of ambrein as a new antinociceptive compound | journal = Japanese Journal of Pharmacology | volume = 60 | issue = 2 | pages = 67–71 | date = October 1992 | pmid = 1479744 | doi = 10.1254/jjp.60.67 | doi-access = free }}</ref> and has been proven to increase sexual behavior in rats,<ref>{{cite journal | vauthors = Taha SA, Islam MW, Ageel AM | title = Effect of ambrein, a major constituent of ambergris, on masculine sexual behavior in rats | journal = Archives Internationales de Pharmacodynamie et de Therapie | volume = 329 | issue = 2 | pages = 283–94 | year = 1995 | pmid = 8540767 }}</ref> providing some support for its traditional aphrodisiac use.
It is a ].


Apart from its supposed aphrodisiac effects, ambrein has been shown to decrease spontaneous contractions of smooth muscles in rats, guinea pigs, and rabbits. It reduces these contractions by serving as an antagonist and interfering with Ca<sup>2+</sup> ions from outside the cell.<ref>{{cite journal | vauthors = Taha SA, Raza M, El-Khawad IE | title = Effect of ambrein on smooth muscle responses to various agonists | journal = Journal of Ethnopharmacology | volume = 60 | issue = 1 | pages = 19–26 | date = February 1998 | pmid = 9533428 | doi = 10.1016/s0378-8741(97)00126-8 }}</ref>
⚫ It has been shown to act as an ]<ref>Taha SA. Studies on the mode of action of ambrein as a new antinociceptive compound. ''Japanese Journal of Pharmacology''. 1992 Oct;60(2):67-71. PMID 1479744</ref> and increase sexual behaviour in rats,<ref>Taha SA, Islam MW, Ageel AM. Effect of ambrein, a major constituent of ambergris, on masculine sexual behavior in rats. ''Archives Internationales de Pharmacodynamie et de Therapie''. 1995 Mar-Apr;329(2):283-94. PMID 8540767</ref> providing some support for its traditional aphrodisiac use.


==References== ==Discovery==
In 1946, ] and Lardon "established that the fragrance of ] is based on the ] (named) ambrein".<ref name=ruzicka46>{{cite journal |doi=10.1002/hlca.19460290414|title=Zur Kenntnis der Triterpene. (105. Mitteilung) Über das Ambreïn, einen Bestandteil des grauen Ambra|year=1946|last1=Ruzicka|first1=L.|last2=Lardon|first2=F.|journal=Helvetica Chimica Acta|volume=29|issue=4|pages=912–921}}</ref><ref name="frs">{{cite journal | last1 = Prelog | first1 = Vladimir | author-link1 = Vladimir Prelog| last2 = Jeger | first2 = Oskar | doi = 10.1098/rsbm.1980.0013 | title = Leopold Ruzicka (13 September 1887 &ndash; 26 September 1976) | journal = ] | volume = 26 | pages = 411–501 | year = 1980 | doi-access = free }}</ref><ref name="hillier19">{{cite journal |doi=10.1530/JOE-19-0084|title=Terpenes, hormones and life: Isoprene rule revisited|year=2019|last1=Hillier|first1=Stephen G.|last2=Lathe|first2=Richard|journal=Journal of Endocrinology|volume=242|issue=2|pages=R9–R22|pmid=31051473|doi-access=free}}</ref>
<references/>

== Biosynthesis ==
Ambrein is synthesized from the common triterpenoid precursor ]. The ] (SHC) catalyzes the cyclization of ] into the monocyclic 3-deoxyachilleol A. ] (BmeTC) converts 3-deoxyachilleol A into the tricyclic ambrein.<ref>{{Cite journal| vauthors = Di K, Qinggele C, Fanglong Z, Ting L, Wenyu L |title=Heterologous biosynthesis of triterpenoid ambrein in engineered Escherichia coli|journal=Biotechnology Letters|volume=40|issue=2|pages= 399–404 |date=February 2018 |doi= 10.1007/s10529-017-2483-2 |pmid=29204767|s2cid=3267910| issn= 1573-6776}}</ref>

== References ==
]
{{reflist}}


] ]
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] ]
] ]
] ]


{{biochem-stub}}

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Latest revision as of 21:54, 22 January 2025

Ambrein
Names
IUPAC name (1R,2R,4aS,8aS)-1-{(3E)-6--4-methylhex-3-en-1-yl}-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
Other names Ambrein
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.784 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C30H52O/c1-22(15-16-24-23(2)13-10-18-27(24,3)4)12-9-14-26-29(7)20-11-19-28(5,6)25(29)17-21-30(26,8)31/h12,24-26,31H,2,9-11,13-21H2,1,3-8H3/b22-12+/t24-,25?,26-,29+,30-/m1/s1Key: BIADSXOKHZFLSN-CQDHYIGWSA-N
  • InChI=1/C30H52O/c1-22(15-16-24-23(2)13-10-18-27(24,3)4)12-9-14-26-29(7)20-11-19-28(5,6)25(29)17-21-30(26,8)31/h12,24-26,31H,2,9-11,13-21H2,1,3-8H3/b22-12+/t24-,25?,26-,29+,30-/m1/s1Key: BIADSXOKHZFLSN-CQDHYIGWBE
SMILES
  • C/C(=C\CC12(CCCC(C2CC1(C)O)(C)C)C)/CC3C(=C)CCCC3(C)C
  • O1(CCC3(1CC\C=C(/C)CC2C(=C)\CCCC2(C)C)(C)CCCC3(C)C)C
Properties
Chemical formula C30H52O
Molar mass 428.745 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale. It has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. Although ambrein itself is odorless, it serves as the biological precursor for aromatic derivatives such as ambroxide and is thought to possess fixative properties for other odorants.

It has been shown to act as an analgesic and has been proven to increase sexual behavior in rats, providing some support for its traditional aphrodisiac use.

Apart from its supposed aphrodisiac effects, ambrein has been shown to decrease spontaneous contractions of smooth muscles in rats, guinea pigs, and rabbits. It reduces these contractions by serving as an antagonist and interfering with Ca ions from outside the cell.

Discovery

In 1946, Ruzicka and Lardon "established that the fragrance of ambergris is based on the triterpene (named) ambrein".

Biosynthesis

Ambrein is synthesized from the common triterpenoid precursor squalene. The squalene-hopene cyclase (SHC) catalyzes the cyclization of squalene into the monocyclic 3-deoxyachilleol A. Tetraprenyl-beta-curcumene synthase (BmeTC) converts 3-deoxyachilleol A into the tricyclic ambrein.

References

Biosynthetic pathway of Ambrein
  1. Sandroni P (October 2001). "Aphrodisiacs past and present: a historical review". Clinical Autonomic Research. 11 (5): 303–7. doi:10.1007/BF02332975. PMID 11758796. S2CID 40455528.
  2. Taha SA (October 1992). "Studies on the mode of action of ambrein as a new antinociceptive compound". Japanese Journal of Pharmacology. 60 (2): 67–71. doi:10.1254/jjp.60.67. PMID 1479744.
  3. Taha SA, Islam MW, Ageel AM (1995). "Effect of ambrein, a major constituent of ambergris, on masculine sexual behavior in rats". Archives Internationales de Pharmacodynamie et de Therapie. 329 (2): 283–94. PMID 8540767.
  4. Taha SA, Raza M, El-Khawad IE (February 1998). "Effect of ambrein on smooth muscle responses to various agonists". Journal of Ethnopharmacology. 60 (1): 19–26. doi:10.1016/s0378-8741(97)00126-8. PMID 9533428.
  5. Ruzicka, L.; Lardon, F. (1946). "Zur Kenntnis der Triterpene. (105. Mitteilung) Über das Ambreïn, einen Bestandteil des grauen Ambra". Helvetica Chimica Acta. 29 (4): 912–921. doi:10.1002/hlca.19460290414.
  6. Prelog, Vladimir; Jeger, Oskar (1980). "Leopold Ruzicka (13 September 1887 – 26 September 1976)". Biogr. Mem. Fellows R. Soc. 26: 411–501. doi:10.1098/rsbm.1980.0013.
  7. Hillier, Stephen G.; Lathe, Richard (2019). "Terpenes, hormones and life: Isoprene rule revisited". Journal of Endocrinology. 242 (2): R9 – R22. doi:10.1530/JOE-19-0084. PMID 31051473.
  8. Di K, Qinggele C, Fanglong Z, Ting L, Wenyu L (February 2018). "Heterologous biosynthesis of triterpenoid ambrein in engineered Escherichia coli". Biotechnology Letters. 40 (2): 399–404. doi:10.1007/s10529-017-2483-2. ISSN 1573-6776. PMID 29204767. S2CID 3267910.
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